(3R,4R,5R,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptane-1,3-diol

Base Information

Chemical Name:(3R,4R,5R,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptane-1,3-diol
CAS No.:157430-98-3
Molecular Formula:C₂₂H₄₀O₄Si
Molecular Weight:396.643
Hs Code.:

Synonyms:(3R,4R,5R,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptane-1,3-diol

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Chemical Property of (3R,4R,5R,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptane-1,3-diol

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Technology Process of (3R,4R,5R,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptane-1,3-diol

There total 10 articles about (3R,4R,5R,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptane-1,3-diol 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: 15.0%

: 179944-93-5
{(2S,3S)-3-[(1R,2R,3R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-oxiranyl}-methanol

: 157430-98-3
(3R,4R,5R,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptane-1,3-diol

: (3R,4R,5R,6R)-7-Benzyloxy-4,6-dimethyl-heptane-1,3,5-triol

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In 1,2-dimethoxyethane; toluene; at 0 ℃; for 2h;
DOI:10.1021/jo9606113

Reference yield:

: 179944-93-5
{(2S,3S)-3-[(1R,2R,3R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-oxiranyl}-methanol

: 157430-98-3
(3R,4R,5R,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptane-1,3-diol

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In 1,2-dimethoxyethane; at 0 ℃; Yield given;
DOI:10.1021/ja00095a072

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 157430-98-3
(3R,4R,5R,6R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-heptane-1,3-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2: 99 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 2 h / -78 °C

3: 1.) potassium tert-butoxide / 1.) THF, room temperature, 1 h, 2.) THF, -78 -> 0 deg C

4: 100 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

5: 96 percent / molecular sieves 4A, titanium tetraisopropoxide, (+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 1 h / -23 °C

6: 74 percent / sodium bis(2-methoxyethoxy)aluminum hydride / 1,2-dimethoxy-ethane; toluene / 2 h / 0 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 A molecular sieve; potassium tert-butylate; diisobutylaluminium hydride; (+)-Weinsaeure-diethylester; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; toluene;
DOI:10.1021/jo9606113