(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

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-enoic acid methyl ester
CAS No.:170706-56-6
Molecular Formula:C₃₂H₄₆O₆Si
Molecular Weight:554.799
Hs Code.:

(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

Synonyms:(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

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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-enoic acid methyl ester

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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-enoic acid methyl ester

There total 5 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-enoic acid methyl ester 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: 90.0%

: 21204-67-1,2605-67-6
methyl (triphenylphosphoranylidene)acetate

: 170706-55-5
[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-acetaldehyde

: 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

Guidance literature:: In benzene; at 50 ℃; for 1h;
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

: 170706-56-6
(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

Guidance literature:: Multi-step reaction with 5 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

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; camphor-10-sulfonic acid; dihydrogen peroxide; potassium 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

: 170706-56-6
(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

Guidance literature:: Multi-step reaction with 4 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

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