2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol

Product Name: 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol
CAS No.: 187590-77-8
Chemical Name: 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol
Synonyms: 1,4-Anhydro-2,3,5-tri-O-benzyl-1-thio-D-ribitol;1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-arabinitol;2,3,5-TRI-O-BENZYL-1,4-DIDEOXY-1,4-EPITHIO-D-ARABINITOL;1,4-Dideoxy-1,4-epithio-2,3,5-tris-O-(phenylmethyl)-D-arabinitol;D-Arabinitol, 1,4-dideoxy-1,4-epithio-2,3,5-tris-O-(phenylmethyl)-;(2R,3S,4S)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydrothiophene
CBNumber: CB52603550
Molecular Formula: C26H28O3S
Formula Weight: 420.56
MOL File: 187590-77-8.mol

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2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol Property

storage temp.: 2-8°C(protect from light)
InChI: InChI=1S/C26H28O3S/c1-4-10-21(11-5-1)16-27-19-25-26(29-18-23-14-8-3-9-15-23)24(20-30-25)28-17-22-12-6-2-7-13-22/h1-15,24-26H,16-20H2/t24-,25-,26+/m1/s1
InChIKey: IISDOLHHPNAZII-CYXNTTPDSA-N
SMILES: C1S[C@H](COCC2=CC=CC=C2)[C@@H](OCC2=CC=CC=C2)[C@@H]1OCC1=CC=CC=C1

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

P280Wear protective gloves/protective clothing/eye protection/face protection.

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

TRC

Product number: B410978
Product name: (2R,3S,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydrothiophene
Packaging: 100mg
Price: $385
Updated: 2021/12/16

AK Scientific

Product number: 9784AA
Product name: (2R,3S,4S)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydrothiophene
Packaging: 100mg
Price: $301
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CRB0005205
Product name: (2R,3S,4S)-3,4-BIS(BENZYLOXY)-2-((BENZYLOXY)METHYL)TETRAHYDROTHIOPHENE
Purity: 95.00%
Packaging: 5MG
Price: $498.39
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CRB0005205
Product name: (2R,3S,4S)-3,4-BIS(BENZYLOXY)-2-((BENZYLOXY)METHYL)TETRAHYDROTHIOPHENE
Purity: 95.00%
Packaging: 1G
Price: $1575
Updated: 2021/12/16

AK Scientific

Product number: 9784AA
Product name: (2R,3S,4S)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydrothiophene
Packaging: 5g
Price: $3921
Updated: 2021/12/16

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2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol Chemical Properties,Usage,Production

Uses

(2R,?3S,?4S)?-?3,?4-?bis(benzyloxy)?-?2-?((benzyloxy)?methyl)?tetrahydrothiophene is an intermediate in the synthesis of Salacinol (S085200), salacinol is a α-glucosidase inhibitor discovered from the herb, Salacia reticulata. Salacinol is used as an antidiabetic agent.

Synthesis

100-39-0

160882-26-8

187590-77-8

At 0 °C, 1.50 g of (2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol was dissolved in 15 mL of N,N-dimethylformamide. To this solution, 2.00 g of 60% sodium hydride was added, the reaction temperature was kept at 5°C or lower and stirred for 1 hour. Subsequently, 4.50 mL of benzyl bromide was slowly added at 0°C. After addition, the reaction mixture was warmed to 25°C and stirring was continued for 3 hours. Upon completion of the reaction, the mixture was extracted by adding ethyl acetate and water to the mixture. The organic layer was separated, washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by column chromatography (eluent: hexane/ethyl acetate = 95/5 to 86/14) to give 2.31 g of (2R,3S,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydrothiophene.

References

[1] Patent: JP2017/214422, 2017, A. Location in patent: Paragraph 0145
[2] Patent: US2017/1974, 2017, A1. Location in patent: Paragraph 0422-0424

2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol Preparation Products And Raw materials

Raw materials

Preparation Products

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2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol Suppliers

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View Lastest Price from 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol manufacturers

Career Henan Chemical Co

Product: 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol 187590-77-8
Price: US $1.00/KG
Min. Order: 1KG
Purity: 97%-99.9%
Supply Ability: 100kg
Release date: 2019-12-25

187590-77-8, 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitolRelated Search:

2,3,5-TRI-O-BENZYL-1,4-DIDEOXY-1,4-EPITHIO-D-ARABINITOL

1,4-Dideoxy-1,4-epithio-2,3,5-tris-O-(phenylmethyl)-D-arabinitol

(2R,3S,4S)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydrothiophene

1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-arabinitol

1,4-Anhydro-2,3,5-tri-O-benzyl-1-thio-D-ribitol

D-Arabinitol, 1,4-dideoxy-1,4-epithio-2,3,5-tris-O-(phenylmethyl)-

187590-77-8