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

Base Information

• Chemical Name: (3aR,5S,6R,6aR)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-6-carbaldehyde
• CAS No.: 141585-50-4
• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.438
• Mol file: 141585-50-4.mol

Synonyms:

Chemical Property of (3aR,5S,6R,6aR)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-6-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5S,6R,6aR)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-6-carbaldehyde

There total 4 articles about (3aR,5S,6R,6aR)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-5-((R)-1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-6-carbaldehyde 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:

(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) → (3aR,5S,6R,6aR)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-6-carbaldehyde (141585-50-4,141660-84-6)

Guidance literature:

With ozone; triphenylphosphine; Multistep reaction; 1) 2) CH₂Cl₂;

DOI:10.1016/0040-4039(90)80138-C

Reference yield:

(2R,3R,4S,5S)-4-<(1S)-1-(hydroxymethyl)ethyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran (119274-25-8,119363-74-5) → (3aR,5S,6R,6aR)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-6-carbaldehyde (141585-50-4,141660-84-6)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH

2: 50percent aq. AcOH

3: 1) O₃ 2) Ph₃P / 1) 2) CH₂Cl₂

With sodium hydride; ozone; acetic acid; triphenylphosphine;

DOI:10.1016/0040-4039(90)80138-C

Reference yield:

(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) → (3aR,5S,6R,6aR)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-6-carbaldehyde (141585-50-4,141660-84-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 50percent aq. AcOH

2: 1) O₃ 2) Ph₃P / 1) 2) CH₂Cl₂

With ozone; acetic acid; triphenylphosphine;

DOI:10.1016/0040-4039(90)80138-C

upstream raw materials:

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

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

Downstream raw materials:

(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

(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

(-)-Acetomycin

Benzoic acid (S)-2-((3aR,5R,6S,6aR)-2,2,5,6-tetramethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-propyl ester