2,2-Dimethyl-propionic acid (R)-2-[(2S,3S,4R)-3-((E)-3-benzyloxy-propenyl)-4,5-dihydroxy-3-methyl-tetrahydro-furan-2-yl]-2-hydroxy-ethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (R)-2-[(2S,3S,4R)-3-((E)-3-benzyloxy-propenyl)-4,5-dihydroxy-3-methyl-tetrahydro-furan-2-yl]-2-hydroxy-ethyl ester
• CAS No.: 116612-18-1
• Molecular Formula: C₂₂H₃₂O₇
• Molecular Weight: 408.492
• Mol file: 116612-18-1.mol

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (R)-2-[(2S,3S,4R)-3-((E)-3-benzyloxy-propenyl)-4,5-dihydroxy-3-methyl-tetrahydro-furan-2-yl]-2-hydroxy-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (R)-2-[(2S,3S,4R)-3-((E)-3-benzyloxy-propenyl)-4,5-dihydroxy-3-methyl-tetrahydro-furan-2-yl]-2-hydroxy-ethyl ester

There total 8 articles about 2,2-Dimethyl-propionic acid (R)-2-[(2S,3S,4R)-3-((E)-3-benzyloxy-propenyl)-4,5-dihydroxy-3-methyl-tetrahydro-furan-2-yl]-2-hydroxy-ethyl 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: 78.0%

(2R,3R,4R,5S)-4-<(E)-3-(benzyloxy)-1-propenyl>-5-<(1R)-<1-hydroxy-2-(2,2-dimethylpropionyl)oxy>ethyl>-2,3-(isopropylidenedioxy)-4-methyltetrahydrofuran (116612-17-0) → 2,2-Dimethyl-propionic acid (R)-2-[(2S,3S,4R)-3-((E)-3-benzyloxy-propenyl)-4,5-dihydroxy-3-methyl-tetrahydro-furan-2-yl]-2-hydroxy-ethyl ester (116612-18-1,116696-90-3)

Guidance literature:

With trifluoroacetic acid; at 5 ℃; for 64h;

DOI:10.1016/S0040-4020(01)82015-9

Reference yield:

(2R,3R,4R,5S)-4-<(E)-3-(benzyloxy)-1-propenyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-methyltetrahydrofuran (116640-23-4) → 2,2-Dimethyl-propionic acid (R)-2-[(2S,3S,4R)-3-((E)-3-benzyloxy-propenyl)-4,5-dihydroxy-3-methyl-tetrahydro-furan-2-yl]-2-hydroxy-ethyl ester (116612-18-1,116696-90-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 50percent CH₃COOH / H₂O

2: 4-DMAP, pyridine

3: 78 percent / 60percent CF₃COOH / H₂O / 0 °C

With pyridine; dmap; acetic acid; trifluoroacetic acid; In water;

DOI:10.1016/S0040-4039(00)80175-6

Reference yield:

3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methyl-3-C-vinyl-α-D-allofuranose (103516-20-7) → 2,2-Dimethyl-propionic acid (R)-2-[(2S,3S,4R)-3-((E)-3-benzyloxy-propenyl)-4,5-dihydroxy-3-methyl-tetrahydro-furan-2-yl]-2-hydroxy-ethyl ester (116612-18-1,116696-90-3)

Guidance literature:

Multi-step reaction with 7 steps

2: 90 percent / benzene / Heating

3: DIBAL-H / CH₂Cl₂ / -40 °C

5: 50percent CH₃COOH / H₂O

6: 4-DMAP, pyridine

7: 78 percent / 60percent CF₃COOH / H₂O / 0 °C

With pyridine; dmap; diisobutylaluminium hydride; acetic acid; trifluoroacetic acid; In dichloromethane; water; benzene;

DOI:10.1016/S0040-4039(00)80175-6

upstream raw materials:

(2R,3R,4R,5S)-4-<(E)-3-(benzyloxy)-1-propenyl>-5-<(1R)-<1-hydroxy-2-(2,2-dimethylpropionyl)oxy>ethyl>-2,3-(isopropylidenedioxy)-4-methyltetrahydrofuran

3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methyl-3-C-vinyl-α-D-allofuranose

(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-6-carbaldehyde

(E)-3-[(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-prop-2-en-1-ol

Downstream raw materials:

[(2R,3S,4S)-3-Benzyloxy-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methoxy-4-methyl-tetrahydro-furan-2-yl]-methanol

2,2-Dimethyl-propionic acid (2R,3S,4S)-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-5-methoxy-4-methyl-tetrahydro-furan-2-ylmethyl ester

2,2-Dimethyl-propionic acid (2R,3S,4S)-3-benzyloxy-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methoxy-4-methyl-tetrahydro-furan-2-ylmethyl ester

Benzoic acid (2R,3S,4R)-4-((4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(2,2-dimethyl-propionyloxymethyl)-5-methoxy-4-methyl-tetrahydro-furan-3-yl ester