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

Base Information

Chemical Name:(E)-4-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-but-2-en-1-ol
CAS No.:170706-57-7
Molecular Formula:C₃₁H₄₆O₅Si
Molecular Weight:526.789
Hs Code.:

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

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

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

There total 6 articles about (E)-4-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-but-2-en-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: 96.0%

: 170706-56-6
(E)-4-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-but-2-enoic acid methyl ester

: 170706-57-7
(E)-4-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-but-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/ja00146a008

Reference yield:

: 131310-62-8
tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-6-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

: 170706-57-7
(E)-4-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / CSA / methanol / 1 h / 0 °C

2: 90 percent / KH / tetrahydrofuran / 1 h / 45 °C

3: 1.) 9-BBN, 2.) 3 N NaOH, 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 1.5 h, 2.) THF, 0 deg C, 1 h

4: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

5: 90 percent / benzene / 1 h / 50 °C

6: 96 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; camphor-10-sulfonic acid; dihydrogen peroxide; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; benzene;
DOI:10.1021/ja00146a008

Reference yield:

: 170706-52-2
(2R,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-6-methyl-6-vinyl-tetrahydro-pyran-3-ol

: 170706-57-7
(E)-4-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / KH / tetrahydrofuran / 1 h / 45 °C

2: 1.) 9-BBN, 2.) 3 N NaOH, 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 1.5 h, 2.) THF, 0 deg C, 1 h

3: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

4: 90 percent / benzene / 1 h / 50 °C

5: 96 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; dihydrogen peroxide; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1021/ja00146a008