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

Base Information

• Chemical Name: methyl (phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronate)
• CAS No.: 850637-29-5
• Molecular Formula: C₂₇H₂₆O₇S
• Molecular Weight: 494.565
• Mol file: 850637-29-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about methyl (phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronate) 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: 91.0%

phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronic acid (850637-28-4) + diazomethane (186581-53-3,908094-01-9,334-88-3) → methyl (phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronate) (850637-29-5)

Guidance literature:

In diethyl ether; N,N-dimethyl-formamide; for 0.0833333h;

DOI:10.1021/ja045613g

Reference yield:

phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranoside (398488-13-6) → methyl (phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronate) (850637-29-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / TEMPO; [bis(acetoxy)iodo]benzene / CH₂Cl₂; H₂O / 0.5 h

2: 91 percent / dimethylformamide; diethyl ether / 0.08 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja045613g

Reference yield:

Benzoic acid (4aR,6S,7R,8S,8aR)-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester → methyl (phenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranosyluronate) (850637-29-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.50 g / aq. TFA / CH₂Cl₂ / 2 h

2: 83 percent / TEMPO; [bis(acetoxy)iodo]benzene / CH₂Cl₂; H₂O / 0.5 h

3: 91 percent / dimethylformamide; diethyl ether / 0.08 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; trifluoroacetic acid; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja045613g

upstream raw materials:

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

diazomethane

thiophenol

1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose

Downstream raw materials:

C₅₁H₄₉N₃O₁₁S

C₅₁H₅₁NO₁₁S

C₅₄H₅₂Cl₃NO₁₃S

C₅₆H₅₃Cl₄NO₁₄S