phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
• CAS No.: 460082-41-1
• Molecular Formula: C₃₃H₃₀O₆S
• Molecular Weight: 554.664
• Mol file: 460082-41-1.mol

Synonyms:phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

There total 10 articles about phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 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: 99.0%

phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside (128848-51-1) + benzoyl chloride (98-88-4) → phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (460082-41-1)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 1h;

DOI:10.1021/acs.orglett.0c02692

Reference yield:

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (71676-30-7,87508-18-7,138922-03-9,87508-17-6) → phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (460082-41-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: di(n-butyl)tin oxide / toluene / 8 h / 110 °C / Inert atmosphere

1.2: 6 h / 60 °C / Inert atmosphere

2.1: pyridine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

With pyridine; di(n-butyl)tin oxide; In tetrahydrofuran; toluene;

DOI:10.1021/jacs.9b11309

Reference yield:

(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) → phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (460082-41-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium methylate / methanol / 1 h / 0 - 20 °C

1.2: Dowex 50w X 8 [H⁺]

2.1: toluene-4-sulfonic acid / acetonitrile / 12 h / 0 - 20 °C

3.1: di(n-butyl)tin oxide / toluene / 12 h / 0 °C / Reflux

3.2: 3 h / 0 - 20 °C

4.1: pyridine / 1 h / 0 - 20 °C

With pyridine; sodium methylate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In methanol; toluene; acetonitrile;

DOI:10.1021/acs.orglett.0c02692

upstream raw materials:

phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

benzoyl chloride

benzoic acid anhydride

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Downstream raw materials:

phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranoside

phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronic acid

methyl (phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronate)

C₅₁H₄₉N₃O₁₁S