(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

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-enoic acid ethyl ester
CAS No.:174968-20-8
Molecular Formula:C₄₁H₆₂O₉Si
Molecular Weight:727.023
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-enoic acid ethyl ester

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-enoic acid ethyl ester

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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-enoic acid ethyl ester

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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-enoic acid ethyl ester

There total 12 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-enoic acid ethyl ester 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:

: 24074-26-8
ethyl (diisopropylphosphoryl)acetate

: [(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]-acetaldehyde

: 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

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; Yield given;
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

: 174968-20-8
(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

Guidance literature:: Multi-step reaction with 12 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

With sodium hydroxide; n-butyllithium; chloro-trimethyl-silane; (Sia)2BH; sulfuric acid; potassium tert-butylate; dihydrogen peroxide; In tetrahydrofuran; diethyl ether;
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

: 174968-20-8
(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

Guidance literature:: Multi-step reaction with 11 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

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