(+)-(2R,3S,4S,6S,7S,8S,9R,10R,11R)-3-hydroxy-1,1:9,11-bis(isopropylidenedioxy)-4,6,8,10-tetramethyl-7-[(1S)-1-phenylethoxy]dodecan-5-one

Base Information

Chemical Name:(+)-(2R,3S,4S,6S,7S,8S,9R,10R,11R)-3-hydroxy-1,1:9,11-bis(isopropylidenedioxy)-4,6,8,10-tetramethyl-7-[(1S)-1-phenylethoxy]dodecan-5-one
CAS No.:1313587-42-6
Molecular Formula:C₃₀H₄₈O₇
Molecular Weight:520.707
Hs Code.:

Synonyms:(+)-(2R,3S,4S,6S,7S,8S,9R,10R,11R)-3-hydroxy-1,1:9,11-bis(isopropylidenedioxy)-4,6,8,10-tetramethyl-7-[(1S)-1-phenylethoxy]dodecan-5-one

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Chemical Property of (+)-(2R,3S,4S,6S,7S,8S,9R,10R,11R)-3-hydroxy-1,1:9,11-bis(isopropylidenedioxy)-4,6,8,10-tetramethyl-7-[(1S)-1-phenylethoxy]dodecan-5-one

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Technology Process of (+)-(2R,3S,4S,6S,7S,8S,9R,10R,11R)-3-hydroxy-1,1:9,11-bis(isopropylidenedioxy)-4,6,8,10-tetramethyl-7-[(1S)-1-phenylethoxy]dodecan-5-one

There total 4 articles about (+)-(2R,3S,4S,6S,7S,8S,9R,10R,11R)-3-hydroxy-1,1:9,11-bis(isopropylidenedioxy)-4,6,8,10-tetramethyl-7-[(1S)-1-phenylethoxy]dodecan-5-one 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: 74.0%

: 1313587-27-7
(1Z,2S,3S,4S,5R,6R,7R)-1-ethylidene-5,7-isopropylidenedioxy-2,4,6-trimethyl-3-[(1S)-1-phenylethoxy]octyl isobutyrate

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: 1313587-42-6
(+)-(2R,3S,4S,6S,7S,8S,9R,10R,11R)-3-hydroxy-1,1:9,11-bis(isopropylidenedioxy)-4,6,8,10-tetramethyl-7-[(1S)-1-phenylethoxy]dodecan-5-one

Guidance literature:: (1Z,2S,3S,4S,5R,6R,7R)-1-ethylidene-5,7-isopropylidenedioxy-2,4,6-trimethyl-3-[(1S)-1-phenylethoxy]octyl isobutyrate; With methyllithium lithium bromide; In diethyl ether; at -78 ℃; for 2h;

2,3-isopropylidene-glyceraldehyde; In diethyl ether; at -78 ℃; for 16h; diastereoselective reaction;
DOI:10.1002/ejoc.201100196

Reference yield:

: C₃₇H₅₉BO₅

: 1313587-42-6
(+)-(2R,3S,4S,6S,7S,8S,9R,10R,11R)-3-hydroxy-1,1:9,11-bis(isopropylidenedioxy)-4,6,8,10-tetramethyl-7-[(1S)-1-phenylethoxy]dodecan-5-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate / methanol; diethyl ether; hexane / 5 h / -78 °C / Inert atmosphere

1.2: 14 h / -5 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / 5 - 20 °C / Inert atmosphere

3.1: methyllithium lithium bromide / diethyl ether / 2 h / -78 °C

3.2: 16 h / -78 °C

With sodium tetrahydroborate; methyllithium lithium bromide; toluene-4-sulfonic acid; In methanol; diethyl ether; hexane;
DOI:10.1002/ejoc.201100196

Reference yield:

: 1313587-26-6
(1Z,2S,3S,4R,5R,6R,7R)-1-ethylidene-5,7-dihydroxy-2,4,6-trimethyl-3-[(1S)-1-phenylethoxy]octyl isobutyrate

: 1313587-42-6
(+)-(2R,3S,4S,6S,7S,8S,9R,10R,11R)-3-hydroxy-1,1:9,11-bis(isopropylidenedioxy)-4,6,8,10-tetramethyl-7-[(1S)-1-phenylethoxy]dodecan-5-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid / 5 - 20 °C / Inert atmosphere

2.1: methyllithium lithium bromide / diethyl ether / 2 h / -78 °C

2.2: 16 h / -78 °C

With methyllithium lithium bromide; toluene-4-sulfonic acid; In diethyl ether;
DOI:10.1002/ejoc.201100196