(3R,6S,8R,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyl-oxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-ol

Base Information

Chemical Name:(3R,6S,8R,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyl-oxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-ol
CAS No.:1466415-08-6
Molecular Formula:C₃₉H₇₂O₅Si₂
Molecular Weight:677.169
Hs Code.:

Synonyms:(3R,6S,8R,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyl-oxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-ol

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Chemical Property of (3R,6S,8R,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyl-oxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-ol

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Technology Process of (3R,6S,8R,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyl-oxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-ol

There total 6 articles about (3R,6S,8R,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyl-oxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-ol 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: 87.0%

: 1466415-09-7
(3R,8S,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyloxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-one

: 1466415-08-6
(3R,6S,8R,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyl-oxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-ol

Guidance literature:: (3R,8S,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyloxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-one; With (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In toluene; at -78 ℃; for 0.0833333h;

With benzo[1,3,2]dioxaborole; In tetrahydrofuran; toluene; at -78 - -20 ℃; for 25h;
DOI:10.1002/chem.201301796

Reference yield: 58.0%

: 1211323-43-1
(R,Z)-((2-ethyl-4-iodopent-3-enyloxy)methyl)benzene

: 1466415-07-5
(3S,5S,7R)-5,7-bis(tert-butyldimethylsilyloxy)-3-methoxy-6,6-dimethyldec-9-enal

: 1466415-08-6
(3R,6S,8R,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyl-oxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-ol

: (R)-(+)-4-(benzyloxymethyl)hexan-2-one

Guidance literature:: (R,Z)-((2-ethyl-4-iodopent-3-enyloxy)methyl)benzene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.5h;

(3S,5S,7R)-5,7-bis(tert-butyldimethylsilyloxy)-3-methoxy-6,6-dimethyldec-9-enal; In diethyl ether; pentane; at -78 ℃; for 18h;
DOI:10.1002/chem.201301796

Reference yield:

: 1466415-07-5
(3S,5S,7R)-5,7-bis(tert-butyldimethylsilyloxy)-3-methoxy-6,6-dimethyldec-9-enal

: 1466415-08-6
(3R,6S,8R,10S,12R,Z)-3-(benzyloxymethyl)-10,12-bis(tert-butyldimethylsilyl-oxy)-8-methoxy-5,11,11-trimethylpentadeca-4,14-dien-6-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C

1.2: 18 h / -78 °C

1.3: 1.5 h / 20 °C

2.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 0.08 h / -78 °C

2.2: 25 h / -78 - -20 °C

With tert.-butyl lithium; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In diethyl ether; toluene; pentane;
DOI:10.1002/chem.201301796