(2S,6S,8S)-2,8-Bis-(2-benzyloxy-ethyl)-10-triisopropylsilanyloxy-1,7-dioxa-spiro[5.5]undec-10-en-4-one

Base Information

Chemical Name:(2S,6S,8S)-2,8-Bis-(2-benzyloxy-ethyl)-10-triisopropylsilanyloxy-1,7-dioxa-spiro[5.5]undec-10-en-4-one
CAS No.:251641-19-7
Molecular Formula:C₃₆H₅₂O₆Si
Molecular Weight:608.891
Hs Code.:

Synonyms:(2S,6S,8S)-2,8-Bis-(2-benzyloxy-ethyl)-10-triisopropylsilanyloxy-1,7-dioxa-spiro[5.5]undec-10-en-4-one

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Chemical Property of (2S,6S,8S)-2,8-Bis-(2-benzyloxy-ethyl)-10-triisopropylsilanyloxy-1,7-dioxa-spiro[5.5]undec-10-en-4-one

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Technology Process of (2S,6S,8S)-2,8-Bis-(2-benzyloxy-ethyl)-10-triisopropylsilanyloxy-1,7-dioxa-spiro[5.5]undec-10-en-4-one

There total 1 articles about (2S,6S,8S)-2,8-Bis-(2-benzyloxy-ethyl)-10-triisopropylsilanyloxy-1,7-dioxa-spiro[5.5]undec-10-en-4-one 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: 64.0%

: 13154-24-0
triisopropylsilyl chloride

: (2S,8S)-2,8-Bis-(2-benzyloxy-ethyl)-1,7-dioxa-spiro[5.5]undecane-4,10-dione

: 251641-19-7
(2S,6S,8S)-2,8-Bis-(2-benzyloxy-ethyl)-10-triisopropylsilanyloxy-1,7-dioxa-spiro[5.5]undec-10-en-4-one

: (2S,6S,8S)-2,8-Bis-(2-benzyloxy-ethyl)-4,10-bis-triisopropylsilanyloxy-1,7-dioxa-spiro[5.5]undeca-3,10-diene

: (2S,8S)-2,8-Bis-(2-benzyloxy-ethyl)-4,10-bis-triisopropylsilanyloxy-1,7-dioxa-spiro[5.5]undeca-4,10-diene

Guidance literature:: (2S,8S)-2,8-Bis-(2-benzyloxy-ethyl)-1,7-dioxa-spiro[5.5]undecane-4,10-dione; With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

triisopropylsilyl chloride; In hexane;
DOI:10.1021/jo9910987

Reference yield: 94.0%

: 251641-19-7
(2S,6S,8S)-2,8-Bis-(2-benzyloxy-ethyl)-10-triisopropylsilanyloxy-1,7-dioxa-spiro[5.5]undec-10-en-4-one

: 251641-21-1
(2S,4S,6R,8S)-2,8-Bis-(2-benzyloxy-ethyl)-10-triisopropylsilanyloxy-1,7-dioxa-spiro[5.5]undec-10-en-4-ol

Guidance literature:: With L-Selectride; In tetrahydrofuran;
DOI:10.1021/jo9910987

Reference yield:

: 251641-19-7
(2S,6S,8S)-2,8-Bis-(2-benzyloxy-ethyl)-10-triisopropylsilanyloxy-1,7-dioxa-spiro[5.5]undec-10-en-4-one

: 251641-31-3
[(2R,4S,6S,8S,10S)-8-[(2S,3R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-hydroxy-3-methyl-4-oxo-butyl]-4-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-10-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 94 percent / L-selectride / tetrahydrofuran

2: 94 percent / TBAF*3H₂O / tetrahydrofuran / -78 °C

3: CeCl₃ / tetrahydrofuran

4: Et₃N / CH₂Cl₂

5: 100 percent / H₂ / Pd(OH)2/C / ethyl acetate

6: 72 percent / LDA / tetrahydrofuran

7: 100 percent / Dess-Martin periodinane

8: aq. camphorsulfonic acid / tetrahydrofuran

9: NaClO₂

10: CH₂Cl₂

11: 100 percent / Dess-Martin periodinane

12: Bu₂BOTf; Et₃N

With sodium chlorite; cerium(III) chloride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; L-Selectride; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate; 1: Reduction / 2: desilylation / 3: Addition / 4: silylation / 5: Hydrogenation / 6: Metallation / 6: silylation / 7: Oxidation / 8: desilylation / 9: Oxidation / 10: Esterification / 11: Oxidation / 12: Addition / 12: Condensation;
DOI:10.1021/jo9910987