(2R,3S,4S,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanoic acid ethyl ester

Base Information

Chemical Name:(2R,3S,4S,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanoic acid ethyl ester
CAS No.:475143-08-9
Molecular Formula:C₂₆H₄₆O₆Si
Molecular Weight:482.733
Hs Code.:

Synonyms:(2R,3S,4S,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanoic acid ethyl ester

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Chemical Property of (2R,3S,4S,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanoic acid ethyl ester

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Technology Process of (2R,3S,4S,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanoic acid ethyl ester

There total 8 articles about (2R,3S,4S,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanoic acid ethyl 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: 81.0%

: 475143-06-7
ethyl (2R,3S,4R,5S,6S)-2-bromo-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6-trimethylheptanoate

: (2S,3S,4S,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanoic acid ethyl ester

: 475143-08-9
(2R,3S,4S,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanoic acid ethyl ester

Guidance literature:: With triethyl borane; tri-n-butyl-tin hydride; magnesium bromide; In dichloromethane; at -78 ℃; for 3h;
DOI:10.1016/S0040-4039(02)01373-4

Reference yield:

: 104701-87-3,115648-41-4,97826-89-6,91751-25-6
3-tert-butyldimethylsilyloxy-2-methylpropanal

: 475143-08-9
(2R,3S,4S,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: chiral oxazaborolidinone from D-TsVal / CH₂Cl₂ / 3 h / -78 °C

2.1: MOMCl; base

2.2: Bu₃SnH; Et₃B / toluene

3.1: 67 percent / TfOH / diethyl ether / 15 h / 20 °C

4.1: 86 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

5.1: 65 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / -78 °C

6.1: 81 percent / Bu₃SnH; Et₃B; MgBr₂*OEt₂ / CH₂Cl₂ / 3 h / -78 °C

With triethyl borane; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; diisobutylaluminium hydride; chloromethyl methyl ether; magnesium bromide; chiral oxazaborolidinone from D-TsVal; In diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(02)01373-4

Reference yield:

: 125244-91-9
3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methylpropan-1-ol

: 475143-08-9
(2R,3S,4S,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-heptanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 82 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: chiral oxazaborolidinone from D-TsVal / CH₂Cl₂ / 3 h / -78 °C

3.1: MOMCl; base

3.2: Bu₃SnH; Et₃B / toluene

4.1: 67 percent / TfOH / diethyl ether / 15 h / 20 °C

5.1: 86 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

6.1: 65 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / -78 °C

7.1: 81 percent / Bu₃SnH; Et₃B; MgBr₂*OEt₂ / CH₂Cl₂ / 3 h / -78 °C

With oxalyl dichloride; triethyl borane; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; diisobutylaluminium hydride; chloromethyl methyl ether; dimethyl sulfoxide; triethylamine; magnesium bromide; chiral oxazaborolidinone from D-TsVal; In diethyl ether; dichloromethane; 1.1: Swern oxidation;
DOI:10.1016/S0040-4039(02)01373-4