(2R,6R,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one

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Chemical Name:(2R,6R,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one
CAS No.:263154-71-8
Molecular Formula:C₂₈H₃₄O₅
Molecular Weight:450.575
Hs Code.:

Synonyms:(2R,6R,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one

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Chemical Property of (2R,6R,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one

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Technology Process of (2R,6R,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one

There total 15 articles about (2R,6R,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-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:

: 3587-60-8
Benzyloxymethyl chloride

: 263154-71-8
(2R,6R,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one

Guidance literature:: Multi-step reaction with 14 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

10.1: [CuIPBu₃]4 / tetrahydrofuran

11.1: 76 percent / L-Selectride / tetrahydrofuran

12.1: 98 percent / KH / tetrahydrofuran

13.1: HF / acetonitrile

14.1: Jones reagent

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; jones reagent; tetrakis{iodo(tributylphosphine)copper(I)}; pH 7 buffer; hydrogen fluoride; titanium tetrachloride; tin(IV) chloride; potassium hydride; L-Selectride; 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; acetonitrile; 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 / 10.1: Addition / 11.1: Reduction / 12.1: Etherification / 13.1: Substitution / 14.1: Oxidation;
DOI:10.1021/ol991345t

Reference yield:

: 63930-49-4
(R)-3-(benzyloxy)-2-methylpropan-1-ol

: 263154-71-8
(2R,6R,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one

Guidance literature:: Multi-step reaction with 13 steps

2: SnCl₄ / CH₂Cl₂

3: NaH / dimethylformamide

4: OsO₄; NaIO₄ / tetrahydrofuran; H₂O

5: 84 percent / LiN(SiMe₃)2 / tetrahydrofuran / -78 °C

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

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

8: 80 percent / TFA / benzene

9: [CuIPBu₃]4 / tetrahydrofuran

10: 76 percent / L-Selectride / tetrahydrofuran

11: 98 percent / KH / tetrahydrofuran

12: HF / acetonitrile

13: Jones reagent

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; jones reagent; tetrakis{iodo(tributylphosphine)copper(I)}; pH 7 buffer; hydrogen fluoride; tin(IV) chloride; potassium hydride; L-Selectride; sodium hydride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene; 1: Oxidation / 2: Addition / 3: Etherification / 4: Oxidation / 5: Addition / 6: Condensation / 7: Hydrolysis / 8: Cyclization / 9: Addition / 10: Reduction / 11: Etherification / 12: Substitution / 13: Oxidation;
DOI:10.1021/ol991345t

Reference yield:

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

: 263154-71-8
(2R,6R,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one

Guidance literature:: Multi-step reaction with 12 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

8: [CuIPBu₃]4 / tetrahydrofuran

9: 76 percent / L-Selectride / tetrahydrofuran

10: 98 percent / KH / tetrahydrofuran

11: HF / acetonitrile

12: Jones reagent

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; jones reagent; tetrakis{iodo(tributylphosphine)copper(I)}; pH 7 buffer; hydrogen fluoride; tin(IV) chloride; potassium hydride; L-Selectride; sodium hydride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene; 1: Addition / 2: Etherification / 3: Oxidation / 4: Addition / 5: Condensation / 6: Hydrolysis / 7: Cyclization / 8: Addition / 9: Reduction / 10: Etherification / 11: Substitution / 12: Oxidation;
DOI:10.1021/ol991345t