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

Base Information

• Chemical Name: (2R,3R,4R,5S)-4-<(E)-3-(benzyloxy)-1-propenyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-methyltetrahydrofuran
• CAS No.: 116640-23-4
• Molecular Formula: C₂₃H₃₂O₆
• Molecular Weight: 404.503
• Mol file: 116640-23-4.mol

Synonyms:

Chemical Property of (2R,3R,4R,5S)-4-<(E)-3-(benzyloxy)-1-propenyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-methyltetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S)-4-<(E)-3-(benzyloxy)-1-propenyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-methyltetrahydrofuran

There total 5 articles about (2R,3R,4R,5S)-4-<(E)-3-(benzyloxy)-1-propenyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-methyltetrahydrofuran 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:

(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 (116612-16-9) + benzyl bromide (100-39-0) → (2R,3R,4R,5S)-4-<(E)-3-(benzyloxy)-1-propenyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-methyltetrahydrofuran (116640-23-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 4h; Yield given;

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

Reference yield:

3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methyl-3-C-vinyl-α-D-allofuranose (103516-20-7) → (2R,3R,4R,5S)-4-<(E)-3-(benzyloxy)-1-propenyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-methyltetrahydrofuran (116640-23-4)

Guidance literature:

Multi-step reaction with 4 steps

2: 90 percent / benzene / Heating

3: DIBAL-H / CH₂Cl₂ / -40 °C

With diisobutylaluminium hydride; In dichloromethane; benzene;

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

Reference yield:

(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 (116612-14-7) → (2R,3R,4R,5S)-4-<(E)-3-(benzyloxy)-1-propenyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-methyltetrahydrofuran (116640-23-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / benzene / Heating

2: DIBAL-H / CH₂Cl₂ / -40 °C

With diisobutylaluminium hydride; In dichloromethane; benzene;

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

upstream raw materials:

(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

benzyl bromide

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

Downstream raw materials:

(2R,3R,4S,5R)-4-(benzoyloxy)-3-<(1R,2R)-<3-(benzyloxy)-1,2-dihydroxy>propyl>-5-<<(2,2-dimethylpropionyl)oxy>methyl>-2-methoxy-3-methyltetrahydrofuran

(2R,3R,4S,5R)-4-(benzoyloxy)-3-<(1S,2S)-<3-(benzyloxy)-1,2-dihydroxy>propyl>-5-<<(2,2-dimethylpropionyl)oxy>methyl>-2-methoxy-3-methyltetrahydrofuran

Benzoic acid (2R,3S,4R,5R)-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

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