3,4,6-tri-O-acetyl-1,2-(1-O-allyl-3,4,6-tri-O-benzyl-2S-β-D-glucopyranos-2-yl)-orthoacetate

Base Information

• Chemical Name: 3,4,6-tri-O-acetyl-1,2-(1-O-allyl-3,4,6-tri-O-benzyl-2S-β-D-glucopyranos-2-yl)-orthoacetate
• CAS No.: 170452-34-3
• Molecular Formula: C₄₄H₅₂O₁₄S
• Molecular Weight: 836.954
• Mol file: 170452-34-3.mol

Synonyms:3,4,6-tri-O-acetyl-1,2-(1-O-allyl-3,4,6-tri-O-benzyl-2S-β-D-glucopyranos-2-yl)-orthoacetate

Chemical Property of 3,4,6-tri-O-acetyl-1,2-(1-O-allyl-3,4,6-tri-O-benzyl-2S-β-D-glucopyranos-2-yl)-orthoacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-tri-O-acetyl-1,2-(1-O-allyl-3,4,6-tri-O-benzyl-2S-β-D-glucopyranos-2-yl)-orthoacetate

There total 3 articles about 3,4,6-tri-O-acetyl-1,2-(1-O-allyl-3,4,6-tri-O-benzyl-2S-β-D-glucopyranos-2-yl)-orthoacetate 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: 79.0%

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) + allyl 3,4,6-tri-O-benzyl-2-thio-β-D-gluco-pyranoside (170452-30-9) → 3,4,6-tri-O-acetyl-1,2-(1-O-allyl-3,4,6-tri-O-benzyl-2S-β-D-glucopyranos-2-yl)-orthoacetate (170452-34-3)

Guidance literature:

With 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; In dimethyl sulfoxide; at -40 ℃; for 2h;

DOI:10.1016/0008-6215(95)00014-K

Reference yield:

allyl 3,4,6-tri-O-benzyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranoside → 3,4,6-tri-O-acetyl-1,2-(1-O-allyl-3,4,6-tri-O-benzyl-2S-β-D-glucopyranos-2-yl)-orthoacetate (170452-34-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / dimethylformamide / 0.08 h / Ambient temperature

2: 97 percent / NaOMe / methanol / 0.08 h / 0 °C

3: 79 percent / 4A molecular sieves, triethylsilyl trifluoromethanesulfonate / dimethylsulfoxide / 2 h / -40 °C

With 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; sodium methylate; In methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(95)00014-K

Reference yield:

allyl 3,4,6-tri-O-benzyl-2-S-acetyl-β-D-glucopyranoside (170452-29-6) → 3,4,6-tri-O-acetyl-1,2-(1-O-allyl-3,4,6-tri-O-benzyl-2S-β-D-glucopyranos-2-yl)-orthoacetate (170452-34-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / NaOMe / methanol / 0.08 h / 0 °C

2: 79 percent / 4A molecular sieves, triethylsilyl trifluoromethanesulfonate / dimethylsulfoxide / 2 h / -40 °C

With 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; sodium methylate; In methanol; dimethyl sulfoxide;

DOI:10.1016/0008-6215(95)00014-K

upstream raw materials:

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

allyl 3,4,6-tri-O-benzyl-2-thio-β-D-gluco-pyranoside

allyl 3,4,6-tri-O-benzyl-2-S-acetyl-β-D-glucopyranoside