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

Base Information

• Chemical Name: (R)-2-Bromo-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propionic acid ethyl ester
• CAS No.: 625109-77-5
• Molecular Formula: C₄₁H₆₅BrO₆Si₂
• Molecular Weight: 790.038
• Mol file: 625109-77-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (R)-2-Bromo-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propionic 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: 73.0%

Dimethoxymethane (109-87-5) + (Z)-(2R,3S,5S,8S,9S,10S)-2-Bromo-9-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3,5-dihydroxy-2,8,10-trimethyl-undec-6-enoic acid ethyl ester (625109-94-6) → (R)-2-Bromo-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propionic acid ethyl ester (625109-77-5)

Guidance literature:

With camphor-10-sulfonic acid;

DOI:10.1021/jo034901c

Reference yield:

2-bromo-1-ethoxy-2-methyl-1-trimethylsilyoxyethene (153645-08-0) → (R)-2-Bromo-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propionic acid ethyl ester (625109-77-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BH₃*THF / CH₂Cl₂; tetrahydrofuran / 1 h / 0 - 20 °C

1.2: 89 percent / CH₂Cl₂; tetrahydrofuran / -78 °C

2.1: 81 percent / DDQ; molecular sieves 4 Angstroem / 5 h / 0 °C

3.1: 73 percent / CSA

With borane-THF; 4 A molecular sieve; camphor-10-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo034901c

Reference yield:

phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate (475051-49-1) → (R)-2-Bromo-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propionic acid ethyl ester (625109-77-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 88 percent / TfOH / 20 °C

2.1: 74 percent / DIBALH / 2 h / -78 °C

3.1: BH₃*THF / CH₂Cl₂; tetrahydrofuran / 1 h / 0 - 20 °C

3.2: 89 percent / CH₂Cl₂; tetrahydrofuran / -78 °C

4.1: 81 percent / DDQ; molecular sieves 4 Angstroem / 5 h / 0 °C

5.1: 73 percent / CSA

With borane-THF; trifluorormethanesulfonic acid; 4 A molecular sieve; camphor-10-sulfonic acid; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation;

DOI:10.1021/jo034901c

upstream raw materials:

Dimethoxymethane

(Z)-(2R,3S,5S,8S,9S,10S)-2-Bromo-9-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-3,5-dihydroxy-2,8,10-trimethyl-undec-6-enoic acid ethyl ester

2-bromo-1-ethoxy-2-methyl-1-trimethylsilyoxyethene

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