Acetic acid (4aR,6S,7R,8S,8aS)-8-benzyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Base Information

• Chemical Name: Acetic acid (4aR,6S,7R,8S,8aS)-8-benzyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• CAS No.: 212134-24-2
• Molecular Formula: C₃₉H₆₄O₁₄Si₂
• Molecular Weight: 813.1

Synonyms:Acetic acid (4aR,6S,7R,8S,8aS)-8-benzyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property of Acetic acid (4aR,6S,7R,8S,8aS)-8-benzyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Acetic acid (4aR,6S,7R,8S,8aS)-8-benzyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

There total 4 articles about Acetic acid (4aR,6S,7R,8S,8aS)-8-benzyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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:

2-(trimethylsilyl)ethyl O-(3-O-benzyl-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside (121377-27-3) → Acetic acid (4aR,6S,7R,8S,8aS)-8-benzyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (212134-24-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / p-TsOH / dimethylformamide / 1.5 h / 5 °C

2: pyridine / 8 h / 0 - 10 °C

3: 1.5 g / pyridine / 16 h / Ambient temperature

With toluene-4-sulfonic acid; In pyridine; N,N-dimethyl-formamide;

DOI:10.1080/07328309808002345

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → Acetic acid (4aR,6S,7R,8S,8aS)-8-benzyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (212134-24-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 8 h / 0 - 10 °C

2: 1.5 g / pyridine / 16 h / Ambient temperature

In pyridine;

DOI:10.1080/07328309808002345

Reference yield:

(2R,3R,4R,5S,6R)-5-((4aR,6S,7R,8R,8aS)-8-Benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,4-diol (122805-11-2) → Acetic acid (4aR,6S,7R,8S,8aS)-8-benzyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (212134-24-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 8 h / 0 - 10 °C

2: 1.5 g / pyridine / 16 h / Ambient temperature

In pyridine;

DOI:10.1080/07328309808002345

upstream raw materials:

acetic anhydride

tert-butyldimethylsilyl chloride

2-(trimethylsilyl)ethyl O-(3-O-benzyl-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside

(2R,3R,4R,5S,6R)-5-((4aR,6S,7R,8R,8aS)-8-Benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,4-diol

Downstream raw materials:

Acetic acid (4aR,6S,7R,8S,8aS)-8-benzyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

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