4-((2R,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-1-[(2S,3R,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

Base Information

Chemical Name:4-((2R,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-1-[(2S,3R,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-but-2-yn-1-ol
CAS No.:455958-50-6
Molecular Formula:C₃₁H₅₀O₇Si
Molecular Weight:562.819
Hs Code.:

4-((2R,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-1-[(2S,3R,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

Synonyms:4-((2R,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-1-[(2S,3R,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

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Chemical Property of 4-((2R,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-1-[(2S,3R,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

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Technology Process of 4-((2R,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-1-[(2S,3R,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

There total 1 articles about 4-((2R,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-1-[(2S,3R,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-but-2-yn-1-ol 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: 88.0%

: 455958-43-7
(2R,3S)-3-Benzyloxy-2-prop-2-ynyl-tetrahydro-pyran

: 455958-49-3
(2R,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-carbaldehyde

: 455958-50-6
4-((2R,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-1-[(2S,3R,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

Guidance literature:: (2R,3S)-3-Benzyloxy-2-prop-2-ynyl-tetrahydro-pyran; With N,N,N,N,N,N-hexamethylphosphoric triamide; tert.-butyl lithium; In tetrahydrofuran; at -78 ℃;

(2R,3R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-carbaldehyde; In tetrahydrofuran; Further stages.;
DOI:10.1021/ol026261q

Reference yield: 99.0%

: 455958-50-6
4-((2R,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-1-[(2S,3R,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

: 455958-52-8
4-((2R,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-1-[(2R,3R,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-but-2-yn-1-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/ol026261q

Reference yield:

: 455958-50-6
4-((2R,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-1-[(2S,3R,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-2-methyl-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

: (4aR,6R,7S,8aR)-2-((2R,3S)-3-Benzyloxy-tetrahydro-pyran-2-ylmethyl)-7-methoxy-6-methoxymethyl-4a-methyl-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b]pyran-4-one

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

2: 43 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Swern oxidation;
DOI:10.1021/ol026261q