(2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester

Base Information

Chemical Name:(2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester
CAS No.:475051-55-9
Molecular Formula:C₄₂H₆₈O₇Si₂
Molecular Weight:741.169
Hs Code.:

(2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester

Synonyms:(2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester

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Chemical Property of (2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester

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Technology Process of (2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester

There total 9 articles about (2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic 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: 80.0%

: (2S,3S,4R)-2-Bromo-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester

: (2S,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester

: 475051-55-9
(2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester

Guidance literature:: With triethyl borane; tri-n-butyl-tin hydride; magnesium bromide; at -78 ℃; for 15h;
DOI:10.1016/S0040-4039(02)01389-8

Reference yield:

: 475051-50-4
(3S,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal

: 475051-55-9
(2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: BH₃*THF / chiral borane from L-TsVal / -78 °C

2: 80 percent / P₂O₅ / CHCl₃ / 1 h / 20 °C

3: 85 percent / Bu₃SnH; Et₃B / toluene / 3 h / -78 °C

4: 90 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

5: TiCl₄ / 0.5 h / -78 °C

6: 80 percent / Bu₃SnH; Et₃B; MgBr₂*OEt₂ / 15 h / -78 °C

With borane-THF; triethyl borane; tri-n-butyl-tin hydride; phosphorus pentoxide; titanium tetrachloride; diisobutylaluminium hydride; magnesium bromide; chiral borane from L-TsVal; In dichloromethane; chloroform; toluene; 5: Mukaiyama aldol reaction;
DOI:10.1016/S0040-4039(02)01389-8

Reference yield:

: 475051-49-1
phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate

: 475051-55-9
(2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 87 percent / 2,6-lutidine / 1 h / 20 °C

2: 80 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

3: 90 percent / (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / -78 - 0 °C

4: BH₃*THF / chiral borane from L-TsVal / -78 °C

5: 80 percent / P₂O₅ / CHCl₃ / 1 h / 20 °C

6: 85 percent / Bu₃SnH; Et₃B / toluene / 3 h / -78 °C

7: 90 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

8: TiCl₄ / 0.5 h / -78 °C

9: 80 percent / Bu₃SnH; Et₃B; MgBr₂*OEt₂ / 15 h / -78 °C

With 2,6-dimethylpyridine; borane-THF; oxalyl dichloride; triethyl borane; tri-n-butyl-tin hydride; phosphorus pentoxide; titanium tetrachloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; magnesium bromide; chiral borane from L-TsVal; In dichloromethane; chloroform; toluene; 3: Swern oxidation / 8: Mukaiyama aldol reaction;
DOI:10.1016/S0040-4039(02)01389-8