2,2-Dimethyl-propionic acid (3R,4R,5R,6R)-7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-heptyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (3R,4R,5R,6R)-7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-heptyl ester
CAS No.:179944-94-6
Molecular Formula:C₂₇H₄₈O₅Si
Molecular Weight:480.761
Hs Code.:

Synonyms:2,2-Dimethyl-propionic acid (3R,4R,5R,6R)-7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-heptyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (3R,4R,5R,6R)-7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-heptyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (3R,4R,5R,6R)-7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-heptyl ester

There total 10 articles about 2,2-Dimethyl-propionic acid (3R,4R,5R,6R)-7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-heptyl 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: 99.0%

: 3282-30-2
pivaloyl chloride

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

: 179944-94-6
2,2-Dimethyl-propionic acid (3R,4R,5R,6R)-7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-heptyl ester

Guidance literature:: With pyridine; at 0 ℃; for 1.5h;
DOI:10.1021/jo9606113

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 179944-94-6
2,2-Dimethyl-propionic acid (3R,4R,5R,6R)-7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-heptyl ester

Guidance literature:: Multi-step reaction with 7 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

7: 99 percent / pyridine / 1.5 h / 0 °C

With pyridine; 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

Reference yield:

: 79026-61-2
(R)-3-benzyloxy-2-methylpropanal

: 179944-94-6
2,2-Dimethyl-propionic acid (3R,4R,5R,6R)-7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4,6-dimethyl-heptyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) dibutylboron triflate, triethylamine / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, -78 -> 0 deg C

2: 1.) trimethylaluminum / 1.) THF, toluene, 0 deg C -> room temperature, 2.) THF, toluene, CH₂Cl₂, -10 -> 0 deg C

3: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

4: 99 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 2 h / -78 °C

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

6: 100 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

7: 96 percent / molecular sieves 4A, titanium tetraisopropoxide, (+)-diethyl tartrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 1 h / -23 °C

8: 74 percent / sodium bis(2-methoxyethoxy)aluminum hydride / 1,2-dimethoxy-ethane; toluene / 2 h / 0 °C

9: 99 percent / pyridine / 1.5 h / 0 °C

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