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

Base Information

• Chemical Name: (2R,4R,6S,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-ol
• CAS No.: 263154-73-0
• Molecular Formula: C₂₈H₃₆O₅
• Molecular Weight: 452.591
• Mol file: 263154-73-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about (2R,4R,6S,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-ol 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: 84.0%

(2R,6R,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-one (263154-71-8) → (2R,4R,6S,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-ol (263154-73-0)

Guidance literature:

With samarium diiodide; isopropyl alcohol; In tetrahydrofuran;

DOI:10.1021/ol991345t

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (2R,4R,6S,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-ol (263154-73-0)

Guidance literature:

Multi-step reaction with 15 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

15.1: 84 percent / SmI₂; i-PrOH / tetrahydrofuran

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; jones reagent; samarium diiodide; 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; isopropyl alcohol; 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 / 15.1: Reduction;

DOI:10.1021/ol991345t

Reference yield:

(R)-3-(benzyloxy)-2-methylpropan-1-ol (63930-49-4) → (2R,4R,6S,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undecan-4-ol (263154-73-0)

Guidance literature:

Multi-step reaction with 14 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

14: 84 percent / SmI₂; i-PrOH / tetrahydrofuran

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; jones reagent; samarium diiodide; tetrakis{iodo(tributylphosphine)copper(I)}; pH 7 buffer; hydrogen fluoride; tin(IV) chloride; potassium hydride; L-Selectride; sodium hydride; isopropyl alcohol; 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 / 14: Reduction;

DOI:10.1021/ol991345t

upstream raw materials:

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

Benzyloxymethyl chloride

(R)-3-(benzyloxy)-2-methylpropan-1-ol

(2S)-3-(benzyloxy)-2-methylpropanal

Downstream raw materials:

[(2R,4R,6R,8R,10S)-10-Benzyloxy-2-((S)-2-benzyloxy-1-methyl-ethyl)-8-vinyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-triisopropyl-silane