2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4-methyl-5-((R)-2-methyl-oxiranyl)-pentyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4-methyl-5-((R)-2-methyl-oxiranyl)-pentyl ester
• CAS No.: 110104-57-9
• Molecular Formula: C₂₁H₃₂O₅
• Molecular Weight: 364.482
• Mol file: 110104-57-9.mol

Synonyms:2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4-methyl-5-((R)-2-methyl-oxiranyl)-pentyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4-methyl-5-((R)-2-methyl-oxiranyl)-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4-methyl-5-((R)-2-methyl-oxiranyl)-pentyl ester

There total 8 articles about 2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4-methyl-5-((R)-2-methyl-oxiranyl)-pentyl ester 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: 79.0%

2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4,6-dimethyl-hept-6-enyl ester (110104-56-8) → 2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4-methyl-5-((R)-2-methyl-oxiranyl)-pentyl ester (110104-57-9)

Guidance literature:

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; In benzene;

DOI:10.1016/S0040-4039(00)85401-5

Reference yield:

1,6:3,4-dianhydro-2-O-tosyl-D-galactose (6167-32-4) → 2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4-methyl-5-((R)-2-methyl-oxiranyl)-pentyl ester (110104-57-9)

Guidance literature:

Multi-step reaction with 8 steps

1: CuI / tetrahydrofuran

2: 80 percent / LiBEt₃H / tetrahydrofuran

3: 94 percent / NaH / n-Bu₄NI

4: BF₃*Et₂O

6: 1.) aq. H₂SO₄ 2.) LiAlH₄ / THF

7: 81 percent / pyridine

8: 79 percent / VO(acac)2, TBHP / benzene

With tert.-butylhydroperoxide; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; sulfuric acid; boron trifluoride diethyl etherate; sodium hydride; lithium triethylborohydride; copper(l) iodide; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; pyridine; benzene;

DOI:10.1016/S0040-4039(00)85401-5

Reference yield:

(1S,2S,3S,4R,5R)-2-methyl-4-<(p-toluenesulfonyl)-oxy>-6,8-dioxabicyclo<3.2.1>octan-3-ol (85433-11-0) → 2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4-methyl-5-((R)-2-methyl-oxiranyl)-pentyl ester (110104-57-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / LiBEt₃H / tetrahydrofuran

2: 94 percent / NaH / n-Bu₄NI

3: BF₃*Et₂O

5: 1.) aq. H₂SO₄ 2.) LiAlH₄ / THF

6: 81 percent / pyridine

7: 79 percent / VO(acac)2, TBHP / benzene

With tert.-butylhydroperoxide; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; sulfuric acid; boron trifluoride diethyl etherate; sodium hydride; lithium triethylborohydride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; pyridine; benzene;

DOI:10.1016/S0040-4039(00)85401-5

upstream raw materials:

2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4,6-dimethyl-hept-6-enyl ester

1,6:3,4-dianhydro-2-O-tosyl-D-galactose

(1S,2S,3S,4R,5R)-2-methyl-4-<(p-toluenesulfonyl)-oxy>-6,8-dioxabicyclo<3.2.1>octan-3-ol

(1S,2S,3R,5R)-3-Benzyloxy-2-methyl-6,8-dioxa-bicyclo[3.2.1]octane

Downstream raw materials:

(4R,5S)-4-((1S,2R)-2-Benzyloxy-1-methyl-butyl)-2,2,5-trimethyl-[1,3]dioxane

2,2-Dimethyl-propionic acid (3R,4R,5R,6S)-3-benzyloxy-5,7-dihydroxy-4,6-dimethyl-heptyl ester