(6S,8R)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undec-2-en-4-one

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Chemical Name:(6S,8R)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undec-2-en-4-one
CAS No.:263154-65-0
Molecular Formula:C₂₅H₃₈O₅Si
Molecular Weight:446.659
Hs Code.:

Synonyms:(6S,8R)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undec-2-en-4-one

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Chemical Property of (6S,8R)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undec-2-en-4-one

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Technology Process of (6S,8R)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undec-2-en-4-one

There total 9 articles about (6S,8R)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undec-2-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: 80.0%

: 263154-64-9
2-[(4R,5S)-6-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-methyl-hexyl]-pyran-4-one

: 263154-65-0
(6S,8R)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undec-2-en-4-one

Guidance literature:: With trifluoroacetic acid; In benzene;
DOI:10.1021/ol991345t

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 263154-65-0
(6S,8R)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undec-2-en-4-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: TiCl₄; DIPEA / CH₂Cl₂

1.2: 95 percent / NaBH₄ / tetrahydrofuran; H₂O

3.1: SnCl₄ / CH₂Cl₂

4.1: NaH / dimethylformamide

5.1: OsO₄; NaIO₄ / tetrahydrofuran; H₂O

6.1: 84 percent / LiN(SiMe₃)2 / tetrahydrofuran / -78 °C

7.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

8.1: DDQ; aq. pH 7 buffer / CH₂Cl₂ / pH 7

9.1: 80 percent / TFA / benzene

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; pH 7 buffer; titanium tetrachloride; tin(IV) chloride; sodium hydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1.1: Alkylation / 1.2: Reduction / 2.1: Oxidation / 3.1: Addition / 4.1: Etherification / 5.1: Oxidation / 6.1: Addition / 7.1: Condensation / 8.1: Hydrolysis / 9.1: Cyclization;
DOI:10.1021/ol991345t

Reference yield:

: 79027-28-4
(2S)-3-(benzyloxy)-2-methylpropanal

: 263154-65-0
(6S,8R)-8-((S)-2-Benzyloxy-1-methyl-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-1,7-dioxa-spiro[5.5]undec-2-en-4-one

Guidance literature:: Multi-step reaction with 7 steps

1: SnCl₄ / CH₂Cl₂

2: NaH / dimethylformamide

3: OsO₄; NaIO₄ / tetrahydrofuran; H₂O

4: 84 percent / LiN(SiMe₃)2 / tetrahydrofuran / -78 °C

5: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

6: DDQ; aq. pH 7 buffer / CH₂Cl₂ / pH 7

7: 80 percent / TFA / benzene

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; pH 7 buffer; tin(IV) chloride; sodium hydride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1: Addition / 2: Etherification / 3: Oxidation / 4: Addition / 5: Condensation / 6: Hydrolysis / 7: Cyclization;
DOI:10.1021/ol991345t