2-[(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]-ethanol

Base Information

Chemical Name:2-[(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]-ethanol
CAS No.:174968-15-1
Molecular Formula:C₃₇H₅₈O₈Si
Molecular Weight:658.948
Hs Code.:

Synonyms:2-[(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]-ethanol

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Chemical Property of 2-[(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]-ethanol

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Technology Process of 2-[(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]-ethanol

There total 10 articles about 2-[(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]-ethanol 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: 45.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 2-[(2S,3S,4S,8S,9S,10S)-8-(2-Hydroxy-ethyl)-3,9-bis-(4-methoxy-benzyloxy)-4,10-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethanol

: 174968-15-1
2-[(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]-ethanol

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; 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

: 174968-15-1
2-[(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]-ethanol

Guidance literature:: Multi-step reaction with 10 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

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

: 174968-15-1
2-[(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]-ethanol

Guidance literature:: Multi-step reaction with 9 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

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