ethyl 6-O-benzoyl-3,4-di-O-benzyl-2-O-methoxymethyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 6-O-benzoyl-3,4-di-O-benzyl-2-O-methoxymethyl-1-thio-β-D-glucopyranoside
• CAS No.: 869639-07-6
• Molecular Formula: C₃₁H₃₆O₇S
• Molecular Weight: 552.689
• Mol file: 869639-07-6.mol

Synonyms:ethyl 6-O-benzoyl-3,4-di-O-benzyl-2-O-methoxymethyl-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 6-O-benzoyl-3,4-di-O-benzyl-2-O-methoxymethyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 6-O-benzoyl-3,4-di-O-benzyl-2-O-methoxymethyl-1-thio-β-D-glucopyranoside

There total 5 articles about ethyl 6-O-benzoyl-3,4-di-O-benzyl-2-O-methoxymethyl-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: 95.0%

ethyl 3,4-di-O-benzyl-2-O-methoxymethyl-1-thio-β-D-glucopyranoside + benzoyl chloride (98-88-4) → ethyl 6-O-benzoyl-3,4-di-O-benzyl-2-O-methoxymethyl-1-thio-β-D-glucopyranoside (869639-07-6)

Guidance literature:

In pyridine; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2005.08.109

Reference yield:

ethyl 4,6-O-benzylidene-3-O-benzyl-2-O-methoxymethyl-1-thio-β-D-glucopyranoside → ethyl 6-O-benzoyl-3,4-di-O-benzyl-2-O-methoxymethyl-1-thio-β-D-glucopyranoside (869639-07-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / triethylsilane; dichlorophenylborane / CH₂Cl₂ / 0.25 h / -78 °C

2: 95 percent / pyridine / 0.5 h / 20 °C

With triethylsilane; phenylborondichloride; In pyridine; dichloromethane;

DOI:10.1016/j.tetlet.2005.08.109

Reference yield:

ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (20701-61-5) → ethyl 6-O-benzoyl-3,4-di-O-benzyl-2-O-methoxymethyl-1-thio-β-D-glucopyranoside (869639-07-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / sodium hdyride / dimethylformamide / 0.5 h / -19 °C

2: 82 percent / P₂O₅ / CH₂Cl₂ / 0.5 h / 20 °C

3: 87 percent / triethylsilane; dichlorophenylborane / CH₂Cl₂ / 0.25 h / -78 °C

4: 95 percent / pyridine / 0.5 h / 20 °C

With triethylsilane; phenylborondichloride; phosphorus pentoxide; sodium hydride; In pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2005.08.109

upstream raw materials:

benzoyl chloride

ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

benzyl bromide

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

Downstream raw materials:

methyl O-(6-O-benzoyl-3,4-di-O-benzyl-2-O-phenylcarbamoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

ethyl 6-O-benzoyl-3,4-di-O-benzyl-2-O-phenylcarbamoyl-1-thio-β-D-glucopyranoside

ethyl 6-O-benzoyl-3,4-di-O-benzyl-1-thio-β-D-glucopyranoside

methyl O-(6-O-benzoyl-3,4-di-O-benzyl-2-O-methoxymethyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside