[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate

Product Name: [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate
CAS No.: 253265-97-3
Chemical Name: [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate
Synonyms: Darunavir int5;Bisfuranolcarbonate;BIS THF HNS Derivative 4;[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-b]furanylSuc;1-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl...;(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate;[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-b]furanyl Succinimidyl Carbonate;[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate;[(3r,3As,6Ar)-Hydroxyhexahydrofuro[2,3-b]furanyl succinimydyl carbonate;(3R,3aS,6aR)-3-Hydroxyhexahydrofuro[2,3-b]furanyl Succinimidyl Carbonate
CBNumber: CB71565749
Molecular Formula: C11H13NO7
Formula Weight: 271.22
MOL File: 253265-97-3.mol

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[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate Property

Melting point:: 122-125℃
Boiling point:: 391.8±52.0 °C(Predicted)
Density: 1.51
vapor pressure: 0-0Pa at 20-25℃
storage temp.: 2-8°C
solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
form: Solid
color: White
InChI: InChI=1S/C11H13NO7/c13-8-1-2-9(14)12(8)19-11(15)18-7-5-17-10-6(7)3-4-16-10/h6-7,10H,1-5H2/t6-,7-,10+/m0/s1
InChIKey: VCFNCYVHQSHFRH-MHYGZLNHSA-N
SMILES: C(O[C@H]1CO[C@@]2([H])OCC[C@]21[H])(=O)ON1C(=O)CCC1=O
LogP: 0.3 at pH7

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TRC

Product number: H942810
Product name: [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-b]furanylSuccinimidylCarbonate
Packaging: 5mg
Price: $110
Updated: 2021/12/16

TRC

Product number: H942810
Product name: [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-b]furanylSuccinimidylCarbonate
Packaging: 500mg
Price: $225
Updated: 2021/12/16

TRC

Product number: H942810
Product name: [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-b]furanylSuccinimidylCarbonate
Packaging: 1g
Price: $375
Updated: 2021/12/16

AK Scientific

Product number: Y6617
Product name: Carbonicacid2,5-dioxo-1-pyrrolidinyl[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl]ester
Packaging: 100mg
Price: $72
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: 10815
Product name: (3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanylSuccinimidylCarbonate
Packaging: 5mg
Price: $890
Updated: 2021/12/16

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[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate Chemical Properties,Usage,Production

Chemical Properties

Pale-Yellow Solid

Uses

Darunavir intermediate.

Synthesis

74124-79-1

156928-09-5

253265-97-3

1. 26.3 g of tert-butyl methyl ether, 35.09 g (135 mmol) of N,N'-disuccinimidyl carbonate, and 20.00 g (73.0% content) of (3R,3aS,6aR)-hexahydrofuro[2,3-B]furan-3-ol were mixed at room temperature, and the mixture was heated to 40 °C. 2. 11.89 g (150 mmol) of pyridine was added slowly and dropwise to the reaction mixture at 40 °C. 3. the reaction mixture was stirred at 40 °C for 22 hours. 4. Upon completion of the reaction, the reaction solution was cooled to 20 °C and 73.0 g of 2-propanol was slowly added dropwise at 20 °C to precipitate the target product 2,5-dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate. 5. The mixture was further cooled to 0-5°C and stirred at that temperature for 19 hours. 6. The precipitated target product was collected by filtration and washed with an appropriate solvent to give 27.83 g of product (97.8% content, 90% yield, enantiomeric excess >99.9% ee). 7. for the isolation of diastereoisomers, 30.0 g of tert-butyl methyl ether, 11.87 g of (3R,3aS,6aR)-hexahydrofuro[2,3-B]furan-3-ol containing 84.3% of the diastereoisomers, and the enzyme (CHIRAZYME L-2c, -flyo, Roche Diagnostics) were mixed at 25°C. 8. 3.31 g (38.4 mmol) of ethyl acetate was added dropwise to the mixture and the insoluble material was removed by filtration after stirring at 25 °C for 40 hours. 9. The filtrate was concentrated to give 12.73 g of a mixture containing (3R,3aS,6aR)-hexahydrofuro[2,3-B]furan-3-ol and its 3S,3aS,6aR isomer (90% yield, diastereoisomer ratio 100.0/0.0).

References

[1] Patent: JP2016/150901, 2016, A. Location in patent: Paragraph 0016; 0017; 0023; 0024
[2] Journal of Organic Chemistry, 2004, vol. 69, # 23, p. 7822 - 7829
[3] European Journal of Organic Chemistry, 2016, vol. 2016, # 10, p. 1874 - 1880
[4] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 1813 - 1822
[5] Patent: WO2010/23322, 2010, A1. Location in patent: Page/Page column 29

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate Preparation Products And Raw materials

Raw materials

Preparation Products

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[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate Suppliers

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View Lastest Price from [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate manufacturers

Anhuyan (Hainan) Biotechnology Co., LTD

Product: [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate 253265-97-3
Price: US $0.00/G/KG
Min. Order: 1G/KG
Purity: 99%
Supply Ability: 10000000KG
Release date: 2025-04-23

Henan Fengda Chemical Co., Ltd

Product: [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate 253265-97-3
Price: US $5.00-0.10/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: g-kg-tons, free sample is available
Release date: 2024-04-16

Hangzhou ICH Biofarm Co., Ltd

Product: [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate 253265-97-3
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 99%HPLC
Supply Ability: 100kg
Release date: 2023-07-04

253265-97-3, [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl CarbonateRelated Search:

3'-Hydroxy Darunavir Hydroxy Darunavir Darunavir Darunavir N-β-D-Glucuronide FURO[3,4-B]FURAN-2(3H)-ONE, TETRAHYDRO-4-METHOXY-, (3AS,4S,6AR)- Darunavir Impurity 19 1-epi-Darunavir Darunavir O-β-D-Glucuronide BIS THF HNS Derivative 3 (3aS,4R,6aR)-Tetrahydro-4-Methoxyfuro[3,4-b]furan-2(3H)-one BIS THF Nitro Derivative 2 4-Hydroxy Darunavir tert-Butyl [(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl[(4-nitrophenyl)sulfonyl]amino]propyl]carbamate Darunavir Darunavir ethanolate (3R,3αS,6αR)-Hexahydrofuro[2,3-β]furan-3-yl-4-nitrophenyl carbonate (2S,3S)-1,2-Epoxy-3-(Boc-amino)-4-phenylbutane 4-AMINO-N-[(2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL]-N-ISOBUTYLBENZENE-1-SULFONAMIDE

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate

1-[[[[(3R,3aS,6aR)-Hexahydrofuro[2,3-β]furan-3-yl]oxy]carbonyl]oxy]-2,5-pyrrolidinedione

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-b]furanyl Succinimidyl Carbonate

1-[[[[(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl]oxy]carbonyl]oxy]-2,5-pyrrolidinedione

Carbonic Acid 2,5-Dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl] Ester

Carbonic Acid 2,5-Dioxo-1-pyrrolidinyl [(3R,3aS,6aR)-Hexahydrofuro[2,3-β]furan-3-yl] Ester

1-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}oxy)pyrrolidine-2,5-dione

(3R,3aS,6aR)-3-Hydroxyhexahydrofuro[2,3-b]furanyl Succinimidyl Carbonate

(3R,3AS,6AR)-3-HYDROXYHEXAHYDROFURO(2,3-B)FURANYL SUCCICINAMIDYL CARBONATE

2,5-Dioxopyrrolidin-1-yl ((3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl) carbonate

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (2,5-dioxopyrrolidin-1-yl) carbonate

carbonic acid 2,5-dioxo-1-pyrrolidinyl ((3r,3as,6ar)-hexahydrofuro(2,3-b)furan-3-yl)

[(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-b]furanylSuc

Bisfuranolcarbonate

BIS THF HNS Derivative 4

Darunavir int5

(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate

Darunavir Intermediate 2,5-Dioxopyrrolidin-l-yl(3R,3aS,6aR)-hexahydro[2,3-b] furan-3- ylcarbonate (For Darunavir Production API)

1-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl...

(3R, 3AS, 6AR) - hydroxyhexahydrofurano [2,3- Β] Furan succinimide carbonate

[(3r,3As,6Ar)-Hydroxyhexahydrofuro[2,3-b]furanyl succinimydyl carbonate

253265-97-3

253565-97-3

Chiral Reagents

Heterocycles

Intermediates