(2R,3R,4S,5S)-4-<(1R)-1-<(benzyloxy)methyl>ethyl>-5-<(1R)-1,2-dihydroxyethyl>-2,3-(isopropylidenedioxy)-4-vinyltetrahydrofuran

Base Information

• Chemical Name: (2R,3R,4S,5S)-4-<(1R)-1-<(benzyloxy)methyl>ethyl>-5-<(1R)-1,2-dihydroxyethyl>-2,3-(isopropylidenedioxy)-4-vinyltetrahydrofuran
• CAS No.: 119274-27-0
• Molecular Formula: C₂₁H₃₀O₆
• Molecular Weight: 378.466
• Mol file: 119274-27-0.mol

Synonyms:

Chemical Property of (2R,3R,4S,5S)-4-<(1R)-1-<(benzyloxy)methyl>ethyl>-5-<(1R)-1,2-dihydroxyethyl>-2,3-(isopropylidenedioxy)-4-vinyltetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5S)-4-<(1R)-1-<(benzyloxy)methyl>ethyl>-5-<(1R)-1,2-dihydroxyethyl>-2,3-(isopropylidenedioxy)-4-vinyltetrahydrofuran

There total 10 articles about (2R,3R,4S,5S)-4-<(1R)-1-<(benzyloxy)methyl>ethyl>-5-<(1R)-1,2-dihydroxyethyl>-2,3-(isopropylidenedioxy)-4-vinyltetrahydrofuran 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: 94.0%

(2R,3R,4S,5S)-4-<(1S)-1-<(benzyloxy)methyl>ethyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran (119274-26-9,119365-49-0) → (2R,3R,4S,5S)-4-<(1S)-1-<(benzyloxy)methyl>ethyl>-5-<(1R)-1,2-dihydroxyethyl>-2,3-(isopropylidenedioxy)-4-vinyltetrahydrofuran (119274-27-0,119363-75-6)

Guidance literature:

With acetic acid; at 35 ℃; for 15h;

DOI:10.1021/jo00266a051

Reference yield: 85.0%

(2R,3R,4S,5S)-4-<(1R)-1-<(benzyloxy)methyl>ethyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran (119274-26-9,119365-49-0) → (2R,3R,4S,5S)-4-<(1R)-1-<(benzyloxy)methyl>ethyl>-5-<(1R)-1,2-dihydroxyethyl>-2,3-(isopropylidenedioxy)-4-vinyltetrahydrofuran (119274-27-0,119363-75-6)

Guidance literature:

With acetic acid; at 35 ℃; for 15h;

DOI:10.1021/jo00266a051

Reference yield:

(2R,3R,4S,5S)-4-<(1S)-1-(ethoxycarbonyl)ethyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran (119274-24-7,119363-73-4) → (2R,3R,4S,5S)-4-<(1S)-1-<(benzyloxy)methyl>ethyl>-5-<(1R)-1,2-dihydroxyethyl>-2,3-(isopropylidenedioxy)-4-vinyltetrahydrofuran (119274-27-0,119363-75-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / LiAlH₄ / tetrahydrofuran / 0.5 h

2: 1.) sodium hydride / 1.) DMF, 0 deg C, 1 h, 2.) RT, 4.5 h

3: 94 percent / 50percent aq. AcOH / 15 h / 35 °C

With lithium aluminium tetrahydride; sodium hydride; acetic acid; In tetrahydrofuran;

DOI:10.1021/jo00266a051

upstream raw materials:

(2R,3R,4S,5S)-4-<(1S)-1-<(benzyloxy)methyl>ethyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran

(2R,3R,4S,5S)-4-<(1S)-1-(hydroxymethyl)ethyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran

(2R,3R,4S,5S)-4-<(1S)-1-(ethoxycarbonyl)ethyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran

benzyl bromide

Downstream raw materials:

(2R,3R,4R,5S)-4-<(1S)-1-<(benzyloxy)methyl>ethyl>-4-formyl-5-(hydroxymethyl)-2,3-(isopropylidenedioxy)tetrahydrofuran

(2R,3R,4R,5S)-4-<(1R)-1-<(benzyloxy)methyl>ethyl>-4-formyl-5-(hydroxymethyl)-2,3-(isopropylidenedioxy)tetrahydrofuran

(3aR,5S,6S,6aR)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-5,6-bis-(bis-ethylsulfanyl-methyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

(3aR,5S,6R,6aR)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5,6-dicarbaldehyde