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

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4,6-dimethyl-hept-6-enyl ester
• CAS No.: 110104-56-8
• Molecular Formula: C₂₁H₃₂O₄
• Molecular Weight: 348.483
• Mol file: 110104-56-8.mol

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

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

There total 7 articles about 2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4,6-dimethyl-hept-6-enyl 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: 81.0%

pivaloyl chloride (3282-30-2) + (3R,4R,5S)-3-Benzyloxy-4,6-dimethyl-hept-6-ene-1,5-diol (110104-55-7) → 2,2-Dimethyl-propionic acid (3R,4R,5S)-3-benzyloxy-5-hydroxy-4,6-dimethyl-hept-6-enyl ester (110104-56-8)

Guidance literature:

In pyridine;

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-4,6-dimethyl-hept-6-enyl ester (110104-56-8)

Guidance literature:

Multi-step reaction with 7 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

With lithium aluminium tetrahydride; sulfuric acid; boron trifluoride diethyl etherate; sodium hydride; lithium triethylborohydride; copper(l) iodide; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; pyridine;

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-4,6-dimethyl-hept-6-enyl ester (110104-56-8)

Guidance literature:

Multi-step reaction with 6 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

With lithium aluminium tetrahydride; sulfuric acid; boron trifluoride diethyl etherate; sodium hydride; lithium triethylborohydride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; pyridine;

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

upstream raw materials:

pivaloyl chloride

(3R,4R,5S)-3-Benzyloxy-4,6-dimethyl-hept-6-ene-1,5-diol

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

Downstream raw materials:

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

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

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