(2R,3R,5R,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal

Base Information

Chemical Name:(2R,3R,5R,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal
CAS No.:625109-84-4
Molecular Formula:C₃₇H₅₈O₅Si₂
Molecular Weight:639.036
Hs Code.:

Synonyms:(2R,3R,5R,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal

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Chemical Property of (2R,3R,5R,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal

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Technology Process of (2R,3R,5R,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal

There total 7 articles about (2R,3R,5R,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal 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: 90.0%

: ethyl (3R,5R,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenoate

: 625109-84-4
(2R,3R,5R,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 2h;
DOI:10.1021/jo034901c

Reference yield:

: 625109-71-9
phenyl (3R,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate

: 625109-84-4
(2R,3R,5R,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal

Guidance literature:: Multi-step reaction with 7 steps

1.1: 87 percent / 2,6-lutidine / 1 h / 20 °C

2.1: 80 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

3.1: 92 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

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

4.2: CH₂Cl₂; tetrahydrofuran / 16 h / -78 °C

5.1: 80 percent / P₂O₅ / CHCl₃ / 3 h / 20 °C

6.1: 89 percent / Bu₃SnH; Et₃B / toluene / 3 h / -78 °C

7.1: 90 percent / DIBAL / CH₂Cl₂; toluene / 2 h / -78 °C

With 2,6-dimethylpyridine; borane-THF; oxalyl dichloride; triethyl borane; tri-n-butyl-tin hydride; phosphorus pentoxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; chloroform; toluene; 3.1: Swern oxidation;
DOI:10.1021/jo034901c

Reference yield:

: 625109-80-0
(3R,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal

: 625109-84-4
(2R,3R,5R,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: CH₂Cl₂; tetrahydrofuran / 16 h / -78 °C

2.1: 80 percent / P₂O₅ / CHCl₃ / 3 h / 20 °C

3.1: 89 percent / Bu₃SnH; Et₃B / toluene / 3 h / -78 °C

4.1: 90 percent / DIBAL / CH₂Cl₂; toluene / 2 h / -78 °C

With borane-THF; triethyl borane; tri-n-butyl-tin hydride; phosphorus pentoxide; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; chloroform; toluene;
DOI:10.1021/jo034901c