[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(benzenesulfonyl)oxan-2-yl]methyl acetate

Base Information

• Chemical Name: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(benzenesulfonyl)oxan-2-yl]methyl acetate
• CAS No.: 53438-23-6
• Molecular Formula: C20H24O11S
• Molecular Weight: 472.47
• DSSTox Substance ID: DTXSID50369553
• Nikkaji Number: J1.379.913J
• Mol file: 53438-23-6.mol

Synonyms:53438-23-6;[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(benzenesulfonyl)oxan-2-yl]methyl acetate;.beta.-D-Glucopyranose, 1-deoxy-1-(phenylsulfonyl)-, tetraacetate;beta-D-Glucopyranose, 1-deoxy-1-(phenylsulfonyl)-, tetraacetate;DTXSID50369553;1-(Phenylsulfonyl)-1-deoxy-beta-D-glucopyranose tetraacetate

Chemical Property of [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(benzenesulfonyl)oxan-2-yl]methyl acetate

Chemical Property:

• PSA: 156.95000
• LogP: 1.62420
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 472.10393275
• Heavy Atom Count: 32
• Complexity: 810

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)S(=O)(=O)C2=CC=CC=C2)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)S(=O)(=O)C2=CC=CC=C2)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(benzenesulfonyl)oxan-2-yl]methyl acetate

There total 5 articles about [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(benzenesulfonyl)oxan-2-yl]methyl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1) → phenylsulfonyl 2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-glucopyranoside (53438-23-6)

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; at 0 ℃; for 0.0833333h;

DOI:10.1071/ch99164

Reference yield: 87.0%

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1) → 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (100432-86-8) + phenylsulfonyl 2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-glucopyranoside (53438-23-6)

Guidance literature:

With urea hydrogen peroxide adduct; In acetic acid; at 80 ℃; for 2h; Time;

DOI:10.3762/bjoc.13.113

Reference yield:

β-D-glucose pentaacetate (604-69-3) → phenylsulfonyl 2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-glucopyranoside (53438-23-6)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 °C / Inert atmosphere

2: urea hydrogen peroxide adduct / acetic acid / 10 h / 20 - 80 °C

With boron trifluoride diethyl etherate; urea hydrogen peroxide adduct; In dichloromethane; acetic acid;

DOI:10.3762/bjoc.13.113

upstream raw materials:

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

β-D-glucose pentaacetate

Downstream raw materials:

D-glucal triacetate

Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-acetoxymethyl-6-benzenesulfonyl-2-bromo-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-benzenesulfonyl-2-bromo-tetrahydro-pyran-3-yl ester

(1S)-1-benzenesulfonyl-1,5-anhydro-D-glucitol