(4R,6S)-4-Benzyloxymethyl-2,2-dimethyl-6-((S)-(R)-1-oxiranyl-allyl)-[1,3]dioxane

Base Information

• Chemical Name: (4R,6S)-4-Benzyloxymethyl-2,2-dimethyl-6-((S)-(R)-1-oxiranyl-allyl)-[1,3]dioxane
• CAS No.: 585535-23-5
• Molecular Formula: C₁₉H₂₆O₄
• Molecular Weight: 318.413
• Mol file: 585535-23-5.mol

Synonyms:(4R,6S)-4-Benzyloxymethyl-2,2-dimethyl-6-((S)-(R)-1-oxiranyl-allyl)-[1,3]dioxane

Chemical Property of (4R,6S)-4-Benzyloxymethyl-2,2-dimethyl-6-((S)-(R)-1-oxiranyl-allyl)-[1,3]dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,6S)-4-Benzyloxymethyl-2,2-dimethyl-6-((S)-(R)-1-oxiranyl-allyl)-[1,3]dioxane

There total 8 articles about (4R,6S)-4-Benzyloxymethyl-2,2-dimethyl-6-((S)-(R)-1-oxiranyl-allyl)-[1,3]dioxane 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: 93.0%

(2R,3R)-3-((4S,6R)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-pent-4-ene-1,2-diol (585535-22-4) → (4R,6S)-4-Benzyloxymethyl-2,2-dimethyl-6-((S)-(R)-1-oxiranyl-allyl)-[1,3]dioxane (585535-23-5)

Guidance literature:

(2R,3R)-3-((4S,6R)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-pent-4-ene-1,2-diol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

With 1-[(2,4,6-triisopropylphenyl)sulfonyl]-1H-imidazole; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo900765p

Reference yield:

(-)-(2S,3S)-2,3-epoxypent-4-en-1-ol (121521-25-3) → (4R,6S)-4-Benzyloxymethyl-2,2-dimethyl-6-((S)-(R)-1-oxiranyl-allyl)-[1,3]dioxane (585535-23-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: imidazole

2.1: hexamethylphosphorotriamide; n-butyllithium / tetrahydrofuran / 1 h / -78 - -45 °C

2.2: tetrahydrofuran / 3 h / -78 - 20 °C

2.3: 2,6-lutidine

3.1: hexamethylphosphorotriamide; t-butyllithium / tetrahydrofuran / 1 h / -78 - -45 °C

3.2: 73 percent / tetrahydrofuran / 3 h / -78 - 20 °C

4.1: 90 percent / mercury(II) perchlorate; 2,6-lutidine / tetrahydrofuran; H₂O

5.1: Et₂BOMe; sodium borohydride / tetrahydrofuran; methanol

6.1: pyridinium p-toluenesulfonate / CH₂Cl₂

7.1: 84 percent / tetra-n-butylammonium fluoride / tetrahydrofuran

8.1: 71 percent / sodium hydride; trisylimidazole / tetrahydrofuran

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; mercury(II) perchlorate; diethyl methoxy borane; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; 1-[(2,4,6-triisopropylphenyl)sulfonyl]-1H-imidazole; In tetrahydrofuran; methanol; dichloromethane; water; 8.1: Fraser-Reid epoxidation;

DOI:10.1021/ol034989g

Reference yield:

(-)-tert-butyldimethyl(((2S,3S)-3-vinyloxiran-2-yl-)methoxy)silane (365562-69-2) → (4R,6S)-4-Benzyloxymethyl-2,2-dimethyl-6-((S)-(R)-1-oxiranyl-allyl)-[1,3]dioxane (585535-23-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: hexamethylphosphorotriamide; n-butyllithium / tetrahydrofuran / 1 h / -78 - -45 °C

1.2: tetrahydrofuran / 3 h / -78 - 20 °C

1.3: 2,6-lutidine

2.1: hexamethylphosphorotriamide; t-butyllithium / tetrahydrofuran / 1 h / -78 - -45 °C

2.2: 73 percent / tetrahydrofuran / 3 h / -78 - 20 °C

3.1: 90 percent / mercury(II) perchlorate; 2,6-lutidine / tetrahydrofuran; H₂O

4.1: Et₂BOMe; sodium borohydride / tetrahydrofuran; methanol

5.1: pyridinium p-toluenesulfonate / CH₂Cl₂

6.1: 84 percent / tetra-n-butylammonium fluoride / tetrahydrofuran

7.1: 71 percent / sodium hydride; trisylimidazole / tetrahydrofuran

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; mercury(II) perchlorate; diethyl methoxy borane; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; 1-[(2,4,6-triisopropylphenyl)sulfonyl]-1H-imidazole; In tetrahydrofuran; methanol; dichloromethane; water; 7.1: Fraser-Reid epoxidation;

DOI:10.1021/ol034989g

upstream raw materials:

(2R,3R)-3-((4S,6R)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-pent-4-ene-1,2-diol

(-)-(2S,3S)-2,3-epoxypent-4-en-1-ol

(-)-tert-butyldimethyl(((2S,3S)-3-vinyloxiran-2-yl-)methoxy)silane

2-{(R)-1-[(R)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-allyl}-[1,3]dithiane

Downstream raw materials:

1-{2-[3-(6-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-[1,3]dithian-2-yl}-5-{2-[2-(tert-butyl-dimethyl-silanyloxy)-3-(2-phenyl-[1,3]dithian-2-yl)-pentyl]-[1,3]dithian-2-yl}-pentan-2-ol

C₅₅H₈₈O₇S₆Si

C₄₇H₈₂O₃S₄Si₃

C₆₆H₁₀₈O₇S₄Si₃