(2E,11E)-(4S,5R,6S,8R,9S,10R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-2,11-diene-1,13-diol

Base Information

Chemical Name:(2E,11E)-(4S,5R,6S,8R,9S,10R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-2,11-diene-1,13-diol
CAS No.:846577-24-0
Molecular Formula:C₄₃H₇₂O₈Si₂
Molecular Weight:773.211
Hs Code.:

Synonyms:(2E,11E)-(4S,5R,6S,8R,9S,10R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-2,11-diene-1,13-diol

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Chemical Property of (2E,11E)-(4S,5R,6S,8R,9S,10R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-2,11-diene-1,13-diol

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Technology Process of (2E,11E)-(4S,5R,6S,8R,9S,10R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-2,11-diene-1,13-diol

There total 9 articles about (2E,11E)-(4S,5R,6S,8R,9S,10R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-2,11-diene-1,13-diol 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: 97.0%

: 846577-33-1
(2E,11E)-(4R,5S,6R,8S,9R,10S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-2,11-dienedioic acid diethyl ester

: 846577-24-0
(2E,11E)-(4S,5R,6S,8R,9S,10R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-2,11-diene-1,13-diol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 1h;
DOI:10.1021/ol0473400

Reference yield:

: (2S,4R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-pentanedial

: 846577-24-0
(2E,11E)-(4S,5R,6S,8R,9S,10R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-2,11-diene-1,13-diol

Guidance literature:: Multi-step reaction with 8 steps

1.1: KHMDS; 18-C-6 / tetrahydrofuran / 0.25 h / -78 °C

1.2: 6.3 g / tetrahydrofuran / -78 - 20 °C

2.1: 100 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: BH₃*THF / tetrahydrofuran / 0.75 h

3.2: 70 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 1 h / 20 °C

4.1: PPTS / CH₂Cl₂ / 20 °C

5.1: 2.03 g / DIBAL / toluene / -78 - 0 °C

6.1: 97 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

7.1: NaH / tetrahydrofuran / -78 °C

7.2: 96 percent / tetrahydrofuran / -78 - 20 °C

8.1: 97 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

With borane-THF; oxalyl dichloride; 18-crown-6 ether; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; 6.1: Swern oxidation / 7.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol0473400

Reference yield:

: 846577-21-7
(2Z,7Z)-(4S,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,8-dimethyl-nona-2,7-diene-1,9-diol

: 846577-24-0
(2E,11E)-(4S,5R,6S,8R,9S,10R)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-trideca-2,11-diene-1,13-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: BH₃*THF / tetrahydrofuran / 0.75 h

1.2: 70 percent / NaBO₃*H₂O / tetrahydrofuran; H₂O / 1 h / 20 °C

2.1: PPTS / CH₂Cl₂ / 20 °C

3.1: 2.03 g / DIBAL / toluene / -78 - 0 °C

4.1: 97 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

5.1: NaH / tetrahydrofuran / -78 °C

5.2: 96 percent / tetrahydrofuran / -78 - 20 °C

6.1: 97 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

With borane-THF; oxalyl dichloride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; 4.1: Swern oxidation / 5.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol0473400