Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,4aR,6R,7R,8S,8aR)-8-(4-chloro-benzyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,4aR,6R,7R,8S,8aR)-8-(4-chloro-benzyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 144533-38-0
• Molecular Formula: C₃₅H₄₁ClO₁₅
• Molecular Weight: 737.155

Synonyms:

Chemical Property of Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,4aR,6R,7R,8S,8aR)-8-(4-chloro-benzyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,4aR,6R,7R,8S,8aR)-8-(4-chloro-benzyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tetrahydro-pyran-3-yl ester

There total 3 articles about Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,4aR,6R,7R,8S,8aR)-8-(4-chloro-benzyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tetrahydro-pyran-3-yl ester 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:

methyl 4,6-O-benzylidene-3-O-(4-chlorobenzyl)-β-D-glucopyranoside (144533-37-9) + β-D-galactose peracetate (4163-60-4) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,4aR,6R,7R,8S,8aR)-8-(4-chloro-benzyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tetrahydro-pyran-3-yl ester (144533-38-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 21h;

DOI:10.1016/0008-6215(93)84002-N

Reference yield:

4-chlorobenzyl bromide (622-95-7) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,4aR,6R,7R,8S,8aR)-8-(4-chloro-benzyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tetrahydro-pyran-3-yl ester (144533-38-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Bu₂SnO, 2.) Bu₄NBr / 1.) benzene, reflux, 2 h, 2.) benzene, reflux, 20 h

2: 4 Angstroem sieves, trimethylsilyl triflate / CH₂Cl₂ / 21 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; di(n-butyl)tin oxide; In dichloromethane;

DOI:10.1016/0008-6215(93)84002-N

Reference yield:

(2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (71117-37-8) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,4aR,6R,7R,8S,8aR)-8-(4-chloro-benzyloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tetrahydro-pyran-3-yl ester (144533-38-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Bu₂SnO, 2.) Bu₄NBr / 1.) benzene, reflux, 2 h, 2.) benzene, reflux, 20 h

2: 4 Angstroem sieves, trimethylsilyl triflate / CH₂Cl₂ / 21 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; di(n-butyl)tin oxide; In dichloromethane;

DOI:10.1016/0008-6215(93)84002-N

upstream raw materials:

methyl 4,6-O-benzylidene-3-O-(4-chlorobenzyl)-β-D-glucopyranoside

β-D-galactose peracetate

4-chlorobenzyl bromide

(2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

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