(R)-2-((1R,2R)-4-(benzyloxy)-1-(methoxymethoxy)-2-methylbutyl)oxirane

Base Information

• Chemical Name: (R)-2-((1R,2R)-4-(benzyloxy)-1-(methoxymethoxy)-2-methylbutyl)oxirane
• CAS No.: 1458033-21-0
• Molecular Formula: C₁₆H₂₄O₄
• Molecular Weight: 280.364
• Mol file: 1458033-21-0.mol

Synonyms:(R)-2-((1R,2R)-4-(benzyloxy)-1-(methoxymethoxy)-2-methylbutyl)oxirane

Chemical Property of (R)-2-((1R,2R)-4-(benzyloxy)-1-(methoxymethoxy)-2-methylbutyl)oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-((1R,2R)-4-(benzyloxy)-1-(methoxymethoxy)-2-methylbutyl)oxirane

There total 13 articles about (R)-2-((1R,2R)-4-(benzyloxy)-1-(methoxymethoxy)-2-methylbutyl)oxirane 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:

4-benzyloxy-butan-1-ol (4541-14-4) → (R)-2-((1R,2R)-4-(benzyloxy)-1-(methoxymethoxy)-2-methylbutyl)oxirane (1458033-21-0)

Guidance literature:

Multi-step reaction with 13 steps

2.1: triethylamine; pivaloyl chloride / tetrahydrofuran / 20 h / -20 °C

2.2: 6 h / 25 °C

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C

4.1: lithium borohydride / ethanol / 0 °C

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / dichloromethane / 4 h / 0 - 20 °C

6.1: pentane; diethyl ether / 2 h / -100 - 0 °C

7.1: N-ethyl-N,N-diisopropylamine / 2 h / 0 - 20 °C

8.1: osmium(VIII) oxide; 2,6-dimethylpyridine; sodium periodate / water; 1,4-dioxane

9.1: D-Prolin / dimethyl sulfoxide / 0.5 h / 20 °C

10.1: sodium tetrahydroborate / ethanol

11.1: copper(ll) sulfate pentahydrate / methanol / 12 h

12.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C

13.1: potassium carbonate / methanol

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium borohydride; copper(ll) sulfate pentahydrate; sodium hexamethyldisilazane; pivaloyl chloride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; D-Prolin; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; pentane; 1.1: |Jones Oxidation;

DOI:10.1016/j.tetlet.2013.08.043

Reference yield:

(4R)-4-benzyl-3-(4-benzyloxy-1-oxobutyl)-2-oxazolidinone (389086-15-1) → (R)-2-((1R,2R)-4-(benzyloxy)-1-(methoxymethoxy)-2-methylbutyl)oxirane (1458033-21-0)

Guidance literature:

Multi-step reaction with 11 steps

1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C

2: lithium borohydride / ethanol / 0 °C

3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / dichloromethane / 4 h / 0 - 20 °C

4: pentane; diethyl ether / 2 h / -100 - 0 °C

5: N-ethyl-N,N-diisopropylamine / 2 h / 0 - 20 °C

6: osmium(VIII) oxide; 2,6-dimethylpyridine; sodium periodate / water; 1,4-dioxane

7: D-Prolin / dimethyl sulfoxide / 0.5 h / 20 °C

8: sodium tetrahydroborate / ethanol

9: copper(ll) sulfate pentahydrate / methanol / 12 h

10: triethylamine / dichloromethane / 3 h / 0 - 20 °C

11: potassium carbonate / methanol

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium borohydride; copper(ll) sulfate pentahydrate; sodium hexamethyldisilazane; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; D-Prolin; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; pentane;

DOI:10.1016/j.tetlet.2013.08.043

Reference yield:

(R)-4-benzyl-3-((R)-4-(benzyloxy)-2-methylbutanoyl) oxazolidin-2-one (1458033-17-4) → (R)-2-((1R,2R)-4-(benzyloxy)-1-(methoxymethoxy)-2-methylbutyl)oxirane (1458033-21-0)

Guidance literature:

Multi-step reaction with 10 steps

1: lithium borohydride / ethanol / 0 °C

2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / dichloromethane / 4 h / 0 - 20 °C

3: pentane; diethyl ether / 2 h / -100 - 0 °C

4: N-ethyl-N,N-diisopropylamine / 2 h / 0 - 20 °C

5: osmium(VIII) oxide; 2,6-dimethylpyridine; sodium periodate / water; 1,4-dioxane

6: D-Prolin / dimethyl sulfoxide / 0.5 h / 20 °C

7: sodium tetrahydroborate / ethanol

8: copper(ll) sulfate pentahydrate / methanol / 12 h

9: triethylamine / dichloromethane / 3 h / 0 - 20 °C

10: potassium carbonate / methanol

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium borohydride; copper(ll) sulfate pentahydrate; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; D-Prolin; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; pentane;

DOI:10.1016/j.tetlet.2013.08.043

upstream raw materials:

(4R)-4-benzyl-3-(4-benzyloxy-1-oxobutyl)-2-oxazolidinone

(R)-4-benzyl-3-((R)-4-(benzyloxy)-2-methylbutanoyl) oxazolidin-2-one

(R)-2-methyl-1,4-butanediol 4-benzyl ether

(4S,5R)-7-(benzyloxy)-5-methylhept-1-en-4-ol

Downstream raw materials:

(5R,6R,Z)-5-((R)-4-(benzyloxy)butan-2-yl)-13,13,14,14-tetramethyl-2,4,12-trioxa-13-silapentadec-8-en-6-ol

(5R,6R)-5-((R)-4-(benzyloxy)butan-2-yl)-13,13,14,14-tetramethyl-2,4,12-trioxa-13-silapentadec-8-yn-6-ol