(R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

Base Information

• Chemical Name: (R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside
• CAS No.: 351030-72-3
• Molecular Formula: C₆₈H₇₅N₃O₁₂Si
• Molecular Weight: 1154.44

Synonyms:(R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

Chemical Property of (R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

Chemical Property:

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Technology Process of (R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

There total 17 articles about (R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-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: 60.2%

(R/S)-But-3-en-2-yl 2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside (351030-49-4) + 2-Azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α,β-D-glucopyranosyl trichloroacetimidate → (R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside (351030-72-3) + (R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In diethyl ether; dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1039/b009845k

Reference yield: 49.6%

(R/S)-But-3-en-2-yl 2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside (351030-49-4) + 2-Azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α,β-D-glucopyranosyl fluoride (351030-70-1) → (R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside (351030-72-3)

Guidance literature:

With zirconocene dichloride; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1039/b009845k

Reference yield: 30.0%

(R/S)-But-3-en-2-yl 2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside (351030-49-4) + (E/Z)-But-2-en-2-yl 2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranoside (351030-64-3) → (R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside (351030-72-3) + (R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In diethyl ether; dichloromethane; at -20 ℃; for 0.5h;

DOI:10.1039/b009845k

upstream raw materials:

(R/S)-But-3-en-2-yl 2-O-benzoyl-3,6-di-O-benzyl-β-D-glucopyranoside

2-Azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-α,β-D-glucopyranosyl fluoride

(E/Z)-But-2-en-2-yl 2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-p-methoxybenzyl-β-D-glucopyranoside

(R/S)-3-buten-2-yl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside

Downstream raw materials:

(R/S)-But-3-en-2-yl 4-O-(2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3,6-di-O-benzoyl-β-D-glucopyranoside

N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-2-[(2R,3R,4R,5R,6R)-4-benzyloxy-2-benzyloxymethyl-5-hydroxy-6-(1-methyl-allyloxy)-tetrahydro-pyran-3-yloxy]-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide

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