1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Base Information

• Chemical Name: 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose
• CAS No.: 100432-86-8
• Molecular Formula: C₂₀H₂₄O₁₀S
• Molecular Weight: 456.471
• Mol file: 100432-86-8.mol

Synonyms:1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Chemical Property of 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

There total 4 articles about 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 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) → 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (100432-86-8)

Guidance literature:

With dihydrogen peroxide; acetic anhydride; silica gel; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1021/jo961478h

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) → 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (100432-86-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / HBr; AcOH / 16 h / 20 °C

2: 30 percent / Bu₄NHSO₄; Na₂CO₃ / ethyl acetate / 20 °C

3: 81 percent / MCPBA / CH₂Cl₂ / 1 h / -70 °C

With hydrogen bromide; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; ethyl acetate;

DOI:10.1055/s-2003-42048

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:

2,6-Dimethoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside