ethyl 3,4,6-tri-O-acetyl-2-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 3,4,6-tri-O-acetyl-2-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
• CAS No.: 946844-12-8
• Molecular Formula: C₄₈H₅₄O₁₄S
• Molecular Weight: 887.014

Synonyms:ethyl 3,4,6-tri-O-acetyl-2-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 3,4,6-tri-O-acetyl-2-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Chemical Property:

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Technology Process of ethyl 3,4,6-tri-O-acetyl-2-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

There total 2 articles about ethyl 3,4,6-tri-O-acetyl-2-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-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: 65.0%

2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (858525-75-4) + ethyl 3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside (98179-07-8) → ethyl 3,4,6-tri-O-acetyl-2-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (946844-12-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In toluene; at -20 - 20 ℃; for 16h;

DOI:10.1021/ol070720b

Reference yield:

2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside (148926-02-7) → ethyl 3,4,6-tri-O-acetyl-2-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (946844-12-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / Cs₂CO₃ / CH₂Cl₂ / 1 h / 20 °C

2: 65 percent / molecular sieves 4 Angstroem; TMSOTf / toluene / 16 h / -20 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; caesium carbonate; In dichloromethane; toluene;

DOI:10.1021/ol070720b

Reference yield: 90.0%

ethyl 3,4,6-tri-O-acetyl-2-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (946844-12-8) → ethyl 2-O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (946844-13-9)

Guidance literature:

With sodium methylate; In methanol; for 1h; Heating;

DOI:10.1021/ol070720b

upstream raw materials:

2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

ethyl 3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside

2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

ethyl 2-O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

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