(2R,3R,5S,6R)-5-Benzyloxy-2-((R)-1-benzyloxy-but-3-enyl)-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol

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Chemical Name:(2R,3R,5S,6R)-5-Benzyloxy-2-((R)-1-benzyloxy-but-3-enyl)-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol
CAS No.:438002-80-3
Molecular Formula:C₃₂H₃₈O₅
Molecular Weight:502.651
Hs Code.:

Synonyms:(2R,3R,5S,6R)-5-Benzyloxy-2-((R)-1-benzyloxy-but-3-enyl)-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3R,5S,6R)-5-Benzyloxy-2-((R)-1-benzyloxy-but-3-enyl)-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol

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Technology Process of (2R,3R,5S,6R)-5-Benzyloxy-2-((R)-1-benzyloxy-but-3-enyl)-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol

There total 9 articles about (2R,3R,5S,6R)-5-Benzyloxy-2-((R)-1-benzyloxy-but-3-enyl)-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-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: 92.0%

: 438002-48-3
[(2S,3R,5S,6R)-5-Benzyloxy-2-((R)-1-benzyloxy-but-3-enyl)-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane

: 438002-80-3
(2R,3R,5S,6R)-5-Benzyloxy-2-((R)-1-benzyloxy-but-3-enyl)-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2.5h;
DOI:10.1021/jo010974p

Reference yield:

: 131310-61-7
(2R,4aR,6S,7R,8aS)-6-Methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 438002-80-3
(2R,3R,5S,6R)-5-Benzyloxy-2-((R)-1-benzyloxy-but-3-enyl)-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 14 h / 20 °C

2.1: p-toluenesulfonic acid hydrate / methanol; CH₂Cl₂ / 19.5 h / 20 °C

3.1: NaH / dimethylformamide / 0.25 h / 20 °C

3.2: 35.53 g / dimethylformamide / 16 h / 20 °C

4.1: 5.53 g / aq. OsO₄; N-methylmorpholine N-oxide / acetone / 19 h / 20 °C

5.1: NaIO₄ / tetrahydrofuran; H₂O / 9 h / 20 °C

6.1: 5.24 g / MgBr₂*Et₂O / CH₂Cl₂ / 2 h / -78 - 20 °C

7.1: NaH / dimethylformamide / 0.5 h / 20 °C

7.2: 100 percent / dimethylformamide / 4.5 h / 0 °C

8.1: 92 percent / TBAF / tetrahydrofuran / 2.5 h / 20 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; magnesium bromide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo010974p

Reference yield:

: 100-39-0
benzyl bromide

: 438002-80-3
(2R,3R,5S,6R)-5-Benzyloxy-2-((R)-1-benzyloxy-but-3-enyl)-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 0.25 h / 20 °C

1.2: 35.53 g / dimethylformamide / 16 h / 20 °C

2.1: 5.53 g / aq. OsO₄; N-methylmorpholine N-oxide / acetone / 19 h / 20 °C

3.1: NaIO₄ / tetrahydrofuran; H₂O / 9 h / 20 °C

4.1: 5.24 g / MgBr₂*Et₂O / CH₂Cl₂ / 2 h / -78 - 20 °C

5.1: NaH / dimethylformamide / 0.5 h / 20 °C

5.2: 100 percent / dimethylformamide / 4.5 h / 0 °C

6.1: 92 percent / TBAF / tetrahydrofuran / 2.5 h / 20 °C

With sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; sodium hydride; 4-methylmorpholine N-oxide; magnesium bromide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo010974p