(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

Base Information

• Chemical Name: (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
• CAS No.: 122805-11-2
• Molecular Formula: C₂₇H₄₄O₁₁Si
• Molecular Weight: 572.725
• Mol file: 122805-11-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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: 85.0%

2-(trimethylsilyl)ethyl O-(3-O-benzyl-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside (121377-27-3) + 2,2-dimethoxy-propane (77-76-9) → (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)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 5 ℃; for 1.5h;

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) → C47H68O23Si

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 8 h / 0 - 10 °C

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

3: 93 percent / TBAF / tetrahydrofuran / 0.25 h / 5 °C

4: 72 percent / Ag₂CO₃, AgClO₄, 4 Angstroem MS / CH₂Cl₂ / 24 h / Ambient temperature

With 4 Angstroem MS; tetrabutyl ammonium fluoride; silver perchlorate; silver carbonate; In tetrahydrofuran; pyridine; dichloromethane;

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-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (212134-25-3)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 8 h / 0 - 10 °C

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

3: 93 percent / TBAF / tetrahydrofuran / 0.25 h / 5 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine;

DOI:10.1080/07328309808002345

upstream raw materials:

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

2,2-dimethoxy-propane

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

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