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

Base Information

Chemical Name:(E)-4-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol
CAS No.:147806-46-0
Molecular Formula:C₃₁H₄₆O₅Si
Molecular Weight:526.789
Hs Code.:

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

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

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

There total 10 articles about (E)-4-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-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: 90.0%

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

: 147806-46-0
(E)-4-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1021/ja00046a063

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 147806-46-0
(E)-4-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 min, 10 min, 2.) CH₂Cl₂, 25 deg C, 1 h

3: benzene / 2 h / 80 °C

4: 90 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; ozone; triphenylphosphine; In dichloromethane; benzene;
DOI:10.1021/ja00046a063

Reference yield:

: 100-39-0
benzyl bromide

: 147806-46-0
(E)-4-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / NaH, n-Bu₄NI / tetrahydrofuran / 24 h / 25 °C

2: 98 percent / 80percent TFA / toluene / 15 h / 0 °C

3: 1.) n-Bu₂SnO, 2.) CsF / 1.) MeOH, 60 deg C, 1.5 h, 2.) DMF 25 deg C, 16 h

4: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

5: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 min, 10 min, 2.) CH₂Cl₂, 25 deg C, 1 h

6: benzene / 2 h / 80 °C

7: 90 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

With 2,6-dimethylpyridine; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; triphenylphosphine; cesium fluoride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene; benzene;
DOI:10.1021/ja00046a063