{(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-methanol

Base Information

Chemical Name:{(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-methanol
CAS No.:147806-47-1
Molecular Formula:C₃₁H₄₆O₆Si
Molecular Weight:542.788
Hs Code.:

{(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-methanol

Synonyms:{(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-methanol

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Chemical Property of {(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-methanol

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Technology Process of {(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-methanol

There total 14 articles about {(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-methanol 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: 98.0%

: 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

: 147806-47-1
{(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-methanol

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; In dichloromethane; at -40 - -20 ℃; for 16h;
DOI:10.1021/ja00046a063

Reference yield: 97.0%

: (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

: 147806-47-1
{(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-methanol

Guidance literature:: With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; iso-butyl hydroperoxide; 4 A molecular sieve; In dichloromethane; at -20 ℃; for 16h;

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 147806-47-1
{(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-methanol

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

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

3: benzene / 2 h / 80 °C

4: 85 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

5: 97 percent / (+)-diethyl tartrate ((+)-DET), Ti(Oi-Pr)4, i-BuOOH, 4A molecular sieves / CH₂Cl₂ / 16 h / -20 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; iso-butyl hydroperoxide; 4 A molecular sieve; diisobutylaluminium hydride; ozone; triphenylphosphine; In dichloromethane; benzene;