(2R,4aR,6S,7S,8S,8aR)-6-Methoxy-2-phenyl-8-trimethylsilanyloxy-7-(3-trimethylsilanyl-prop-2-ynyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

• Chemical Name: (2R,4aR,6S,7S,8S,8aR)-6-Methoxy-2-phenyl-8-trimethylsilanyloxy-7-(3-trimethylsilanyl-prop-2-ynyl)-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS No.: 131529-40-3
• Molecular Formula: C₂₃H₃₆O₅Si₂
• Molecular Weight: 448.707

Synonyms:(2R,4aR,6S,7S,8S,8aR)-6-Methoxy-2-phenyl-8-trimethylsilanyloxy-7-(3-trimethylsilanyl-prop-2-ynyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property of (2R,4aR,6S,7S,8S,8aR)-6-Methoxy-2-phenyl-8-trimethylsilanyloxy-7-(3-trimethylsilanyl-prop-2-ynyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property:

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Technology Process of (2R,4aR,6S,7S,8S,8aR)-6-Methoxy-2-phenyl-8-trimethylsilanyloxy-7-(3-trimethylsilanyl-prop-2-ynyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 2 articles about (2R,4aR,6S,7S,8S,8aR)-6-Methoxy-2-phenyl-8-trimethylsilanyloxy-7-(3-trimethylsilanyl-prop-2-ynyl)-hexahydro-pyrano[3,2-d][1,3]dioxine 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 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside (66537-92-6) → (2R,4aR,6S,7S,8S,8aR)-6-Methoxy-2-phenyl-8-trimethylsilanyloxy-7-(3-trimethylsilanyl-prop-2-ynyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (131529-40-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) BuLi / 1.) THF, hexane, 30 min, 2.) RT, 2.5 h

2: 1.) BuLi / 1.) THF, 30 min, 2.) 1 h

With n-butyllithium;

DOI:10.1071/CH9901681

Reference yield:

chloro-trimethyl-silane (75-77-4) + methyl 4,6-O-benzylidene-2-deoxy-2-C-(prop-2-ynyl)-α-D-altroside (131529-37-8) → (2R,4aR,6S,7S,8S,8aR)-6-Methoxy-2-phenyl-8-trimethylsilanyloxy-7-(3-trimethylsilanyl-prop-2-ynyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (131529-40-3)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, 30 min, 2.) 1 h;

DOI:10.1071/CH9901681

Reference yield: 94.0%

(2R,4aR,6S,7S,8S,8aR)-6-Methoxy-2-phenyl-8-trimethylsilanyloxy-7-(3-trimethylsilanyl-prop-2-ynyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (131529-40-3) → methyl 4,6-O-benzylidene-2-deoxy-2-C-(3-trimethylsilylprop-2-ynyl)-α-D-altroside (131529-36-7)

Guidance literature:

With camphor-10-sulfonic acid; In tetrahydrofuran; water;

DOI:10.1071/CH9901681

upstream raw materials:

chloro-trimethyl-silane

methyl 4,6-O-benzylidene-2-deoxy-2-C-(prop-2-ynyl)-α-D-altroside

methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside

Downstream raw materials:

methyl 4,6-O-benzylidene-2-deoxy-2-C-(3-trimethylsilylprop-2-ynyl)-α-D-altroside

(2R,4aR,6S,7S,8S,8aS)-8-Benzyloxy-6-methoxy-2-phenyl-7-prop-2-ynyl-hexahydro-pyrano[3,2-d][1,3]dioxine

[3-((2R,4aR,6S,7S,8S,8aS)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-prop-1-ynyl]-trimethyl-silane

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