(E)-4-[(2S,3S,4S,6R,8S,9S,10S)-8-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-but-2-en-1-ol

Base Information

Chemical Name:(E)-4-[(2S,3S,4S,6R,8S,9S,10S)-8-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-but-2-en-1-ol
CAS No.:174968-06-0
Molecular Formula:C₃₉H₆₀O₈Si
Molecular Weight:684.986
Hs Code.:

(E)-4-[(2S,3S,4S,6R,8S,9S,10S)-8-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-but-2-en-1-ol

Synonyms:(E)-4-[(2S,3S,4S,6R,8S,9S,10S)-8-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-but-2-en-1-ol

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Chemical Property of (E)-4-[(2S,3S,4S,6R,8S,9S,10S)-8-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-but-2-en-1-ol

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Technology Process of (E)-4-[(2S,3S,4S,6R,8S,9S,10S)-8-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-but-2-en-1-ol

There total 13 articles about (E)-4-[(2S,3S,4S,6R,8S,9S,10S)-8-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-but-2-en-1-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: 99.0%

: 174968-20-8
(E)-4-[(2S,3S,4S,6R,8S,9S,10S)-8-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-but-2-enoic acid ethyl ester

: 174968-06-0
(E)-4-[(2S,3S,4S,6R,8S,9S,10S)-8-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-but-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;
DOI:10.3987/COM-95-S30

Reference yield:

: 174968-09-3
(R)-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-(4-methoxy-benzyloxy)-acetaldehyde

: 174968-06-0
(E)-4-[(2S,3S,4S,6R,8S,9S,10S)-8-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 13 steps

1: nBuLi / tetrahydrofuran / -78 °C

2: TMSCl / tetrahydrofuran; diethyl ether / -20 °C

3: 89 percent / nBuLi / tetrahydrofuran / -78 °C

4: 96 percent / nBuLi / tetrahydrofuran / -78 °C

5: 98 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C

6: 75 percent / 6N H₂SO₄ / tetrahydrofuran / Ambient temperature

7: Swern oxidation

8: tBuOK / tetrahydrofuran / -78 - 0 °C

9: 1.) (Sia)2BH; 2.) H₂O₂, NaOH / 1.) -20 deg C; 2.) THF

10: 45 percent / tBuOK / tetrahydrofuran / -78 °C

11: Swern oxidation

12: tBuOK / tetrahydrofuran / -78 °C

13: 99 percent / DIBAH / CH₂Cl₂ / -78 °C

With sodium hydroxide; n-butyllithium; chloro-trimethyl-silane; (Sia)2BH; sulfuric acid; potassium tert-butylate; dihydrogen peroxide; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.3987/COM-95-S30

Reference yield:

: 596092-70-5
(E)-(S)-4-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-but-2-enoic acid methyl ester

: 174968-06-0
(E)-4-[(2S,3S,4S,6R,8S,9S,10S)-8-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 12 steps

1: TMSCl / tetrahydrofuran; diethyl ether / -20 °C

2: 89 percent / nBuLi / tetrahydrofuran / -78 °C

3: 96 percent / nBuLi / tetrahydrofuran / -78 °C

4: 98 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C

5: 75 percent / 6N H₂SO₄ / tetrahydrofuran / Ambient temperature

6: Swern oxidation

7: tBuOK / tetrahydrofuran / -78 - 0 °C

8: 1.) (Sia)2BH; 2.) H₂O₂, NaOH / 1.) -20 deg C; 2.) THF

9: 45 percent / tBuOK / tetrahydrofuran / -78 °C

10: Swern oxidation

11: tBuOK / tetrahydrofuran / -78 °C

12: 99 percent / DIBAH / CH₂Cl₂ / -78 °C

With sodium hydroxide; n-butyllithium; chloro-trimethyl-silane; (Sia)2BH; sulfuric acid; potassium tert-butylate; dihydrogen peroxide; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.3987/COM-95-S30