2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate)

Product Name: 2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate)
CAS No.: 4330-21-6
Chemical Name: 2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate)
Synonyms: 1-Chloro-2-deoxy-3,5-di-O-(4-toluoyl)-alpha-D-ribofuranose;NSC 148837;Hoffer's chlorosugar;Hoffer's alpha-chlorosugar;Hoffer's Chlorosugar (~90%);Di-P-Toluoyl-Pentafuranosyl-Chloride;3,5-bis(toluoyl)-2-deoxyribosyl chloride;1-CHLORO-3,5-BIS[O-(4-TOLUOYL)]-2-DEOXYRIBOSE;3,5-di-O-(P-toluyl)-2-deoxy-D-*ribofuranosyl chlo;1-Chloro-3,5-di-O-toluoyl-2-deoxy-a-D-ribofuranose
CBNumber: CB2231583
Molecular Formula: C21H21ClO5
Formula Weight: 388.84
MOL File: 4330-21-6.mol

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2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate) Property

Melting point:: 117-119 °C
Boiling point:: 518.4±50.0 °C(Predicted)
Density: 1.28
storage temp.: Sealed in dry,Store in freezer, under -20°C
solubility: Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly, Sonicated), Methanol
form: Solid
color: Off-White to Light Grey
Stability:: Moisture Sensitive
InChI: InChI=1/C21H21ClO5/c1-13-3-7-15(8-4-13)20(23)25-12-18-17(11-19(22)26-18)27-21(24)16-9-5-14(2)6-10-16/h3-10,17-19H,11-12H2,1-2H3/t17-,18+,19+/s3
InChIKey: XJHDINDXQMZBKW-XUVXKRRUSA-N
SMILES: [C@@H]1(Cl)O[C@H](COC(=O)C2=CC=C(C)C=C2)[C@@H](OC(=O)C2=CC=C(C)C=C2)C1 |&1:0,3,15,r|

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 3
HS Code: 29321900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: D7283
Product name: 3,5-Di-O-(p-toluyl)-2-deoxy-D-ribofuranosyl chloride
Purity: ~90%
Packaging: 1g
Price: $935
Updated: 2025/07/31

TCI Chemical

Product number: D5631
Product name: 2-Deoxy-3,5-O-di-p-toluoyl-α-D-erythro-pentofuranosyl Chloride
Packaging: 1G
Price: $38
Updated: 2021/12/16

TCI Chemical

Product number: D5631
Product name: 2-Deoxy-3,5-O-di-p-toluoyl-α-D-erythro-pentofuranosyl Chloride
Packaging: 5G
Price: $188
Updated: 2021/12/16

TRC

Product number: H456650
Product name: Hoffer''sChlorosugar(~90%)
Packaging: 5g
Price: $105
Updated: 2021/12/16

TRC

Product number: H456650
Product name: Hoffer''sChlorosugar(~90%)
Packaging: 25g
Price: $340
Updated: 2021/12/16

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2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate) Chemical Properties,Usage,Production

Chemical Properties

White solid

Uses

Hoffer''s Chlorosugar is a synthetic precursor for ribose glycosides and ribonucleosides.

Synthesis

4330-34-1

4330-21-6

Under argon protection, (2R,3S)-5-methoxy-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (50.0 g, 0.13 mol) was dissolved in glacial acetic acid (150 mL) and stirred at room temperature for 20 min. The reaction solution was cooled to 10-15 °C and a dioxane solution (150 mL, 0.6 mol) in 4 M HCl was slowly added dropwise for a controlled time of 5 min. After observing a light straw color to the solution, a small amount of 1-Α-chloro-3,5-di-O-tosyl-2-deoxy-D-ribofuranose crystal species was added and stirred briefly until a precipitate appeared. Stirring was stopped and the reaction mixture was allowed to stand for 40 minutes while being kept cool with an ice water bath. The white slurry was broken up by swirling the flask and quickly filtered. The resulting filter cake was washed with cold ether (3 x 30 mL) and dried under high vacuum to afford the target product 1-Α-chloro-3,5-di-O-p-toluoyl-2-deoxy-D-ribofuranose (34.1 g, 67% yield) as a white solid. The spectral data and analytical results of the product were in agreement with those reported in the literature. Thin layer chromatography (TLC) Rf value was 0.58 (Expanding agent: ethyl acetate-hexane, 1:2). Infrared spectra (IR, cm-1): 3030, 2951, 1708, 1276, 1178, 1099, 755. nuclear magnetic resonance hydrogen spectrum (1H NMR, 250.1 MHz, CDCl3): δ 2.41 (s, 3H, CH3), 2.42 (s, 3H, CH3), 2.74 (m, 1H, 2-CH), 2.84 (m 1H, 2-CH), 4.61 (dd, J=12.1,4.1 Hz, 1H, 5-CH), 4.66 (dd, J=12.1,4.1 Hz, 1H, 5-CH), 4.85 (m, 1H, 4-CH), 5.58 (m, 1H, 3-CH), 6.47 (d, J=4.2 Hz, 1H, 1-CH), 7.24 (d, J=8.3 Hz, 2H, 3,5-tol-CH), 7.26 (d, J=8.3 Hz, 2H, 3,5-tol-CH), 7.90 (d, J=8.3 Hz, 2H, 2,6-tol-CH), 7.99 (d, J=8.3 Hz, 2H, 2,6-tol-CH). Nuclear magnetic resonance carbon spectrum (13C NMR, 62.9 MHz, CDCl3): δ 21.70 (CH3), 21.71 (CH3), 44.54 (2-CH2), 63.51 (5-CH2), 73.56 (4-CH), 84.71 (3-CH), 95.3 (1-CH), 126.66 (C), 126.72 ( C), 129.19 (CH), 129.21 (CH), 129.63 (CH), 129.88 (CH), 144.07 (C), 144.30 (C), 166.07 (CO), 166.41 (CO). Mass spectra (EI): m/z (relative abundance) 353 ([M-Cl]+, 1), 252 (1), 216 (32), 136 (38), 119 (100), 91 (78), 81 (100), 65 (28), 53 (25), 39 (19). Calculated elemental analysis (C21H22ClO5): C, 64.8; H, 5.41. Measured values: C, 64.4; H, 5.39.

References

[1] Organic and Biomolecular Chemistry, 2003, vol. 1, # 13, p. 2267 - 2275
[2] Organic Letters, 2002, vol. 4, # 26, p. 4571 - 4574
[3] Journal of the Chinese Chemical Society, 1997, vol. 44, # 4, p. 413 - 416
[4] Arkivoc, 2017, vol. 2017, # 3, p. 87 - 104
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 8, p. 2044 - 2050

2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate) Preparation Products And Raw materials

Raw materials

Preparation Products

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2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate) Suppliers

Americas 1 Austria 1 China 136 Europe 1 India 4 Japan 2 Switzerland 1 United Kingdom 7 United States 12 Global 165

TOKYO CHEMICAL INDUSTRY CO., LTD.

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Wako Pure Chemical Industries, Ltd.

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View Lastest Price from 2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate) manufacturers

Henan Aochuang Chemical Co.,Ltd.

Product: 2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate) 4330-21-6
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1Ton
Release date: 2022-09-29

Henan Fengda Chemical Co., Ltd

Product: 2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate) 4330-21-6
Price: US $5.00-0.10/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: g-kg-tons, free sample is available
Release date: 2024-03-27

Career Henan Chemical Co

Product: 3,5-Di-O-(p-toluyl)-2-deoxy-D-ribofuranosyl chloride 4330-21-6
Price: US $150.00/KG
Min. Order: 1KG
Purity: 985
Supply Ability: 500KG
Release date: 2018-08-03

4330-21-6, 2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate)Related Search:

ALPHA-L-ERYTHRO-PENTOFURANOSYL CHLORIDE-2-DEOXY-BIS(4-METHYL BENZOATE) 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose 1-Chloro-3,5-di(4-chlorbenzoyl)-2-deoxy-D-ribose 1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose Brivudine

1-Chloro-2-deoxy-3,5-di-O-(4-toluoyl)-alpha-D-ribofuranose

α-D-erythro-Pentofuranosylchloride, 2-deoxy-, 3,5-bis(4-Methylbenzoate)

3,5-bis(toluoyl)-2-deoxyribosyl chloride

1-α-Chloro-3,5-di-O-(4-toluoyl) -2-deoxy-D-ribofuranose

3,5-DI-O-(P-TOLUYL)-2-DEOXY-ALPHA-D-RIBOFURANOSYL CHLORIDE

1-CHLORO-3,5-BIS[O-(4-TOLUOYL)]-2-DEOXYRIBOSE

.alpha.-D-erythro-Pentofuranosyl chloride, 2-deoxy-, bis(4-methylbenzoate)

1-Chloro-3,5-di-O-toluoyl-2-deoxy-a-D-ribofuranose

3,5-DI-O-(P-TOLUYL)-2-DEOXY-D-RIBOFURANOSYL CHLORIDE, >95%

3,5-Di-O-p-toluyl-2-deoxy-a-D-ribofuranosyl chloride

3,5-di-O-(P-toluyl)-2-deoxy-D-*ribofuranosyl chlo

2-deoxydi(p-toluoyl)-alpha-D-erythro-pentofuranosyl chloride

3,5-DI-O-(P-TOLUYL)-2-DEOXY-D-*RIBOFURAN OSYL CHLORI

1-CHLORO-3,5-DI-O-TOLUOYL-2-DEOXY-ALPHA-D-RIBOFURANOSE

1-Chloro-2-deoxy-3,5-di-O-toluoyl-a-D-ribofuranose

1-Chloro-2-deoxy-3,5-di-O-p-toluoyl-alpha-D-ribose

2-Deoxy-3,5-di-O-p-toluoyl-alpha-D-erythro-pentofuranosyl chloride

2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate)

Hoffer's alpha-chlorosugar

Hoffer's chlorosugar

NSC 148837

1-Chloro-3-O,5-O-di-p-toluoyl-1,2-dideoxy-D-ribofuranose

1-Chloro-3-O,5-O-bis(4-methylbenzoyl)-1,2-dideoxy-α-D-erythro-pentofuranose

2-Deoxy-3-O,5-O-bis(4-methylbenzoyl)-α-D-erythro-pentofuranosyl chloride

3-O,5-O-Bis(4-methylbenzoyl)-2-deoxy-α-D-erythro-pentofuranosyl chloride

3-O,5-O-Bis(4-methylbenzoyl)-2-deoxy-α-D-ribofuranosyl chloride

3-O,5-O-Di-p-toluoyl-2-deoxy-α-D-erythro-pentofuranosyl chloride

3-O,5-O-Di-p-toluoyl-2-deoxy-α-D-ribofuranosyl chloride

2-Deoxy-3,5-O-di-p-toluoyl-alpha-D-erythro-pentofuranosyl Chloride

[(2R,3S,5R)-5-chloro-3-(4-methylbenzoyloxy)oxolan-2-yl]methyl 4-methylbenzoate

(2R,3S,5R)-5-Chloro-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

Hoffer's Chlorosugar (~90%)

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate) USP/EP/BP

a-D-erythro-Pentofuranosylchloride, 2-deoxy-, 3,5-bis(4-methylbenzoate

3,5-Di-O-toluoyl-α-1-chloro-2-deoxy-D-ribofuranose

α-D-erythro-Pentofuranosyl chloride, 2-deoxy-, 3,5-bis(4-methylbenzoate)

Di-P-Toluoyl-Pentafuranosyl-Chloride

1-A-Chloro-3,5-di-O-p-toluoyl-2-deoxy-D-ribofuranose

3,5-Di-O-(p-toluyl)-2-deoxy-<sc>D</sc>-ribofuranosyl chloride

2-Deoxy-alpha-D-erythrope ntofuranosyl chloride 3,5-bis(4-methyIbenzoate)

4330-21-6

C21Cl1H21O5

C21H21ClO6

C21H21ClO5

Monosaccharide

Carbohydrates

Biochemicals and Reagents

BioChemical

Carbohydrates D-FBiochemicals and Reagents

Monosaccharide

Carbohydrates

Carbohydrates A to