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

Base Information

• Chemical Name: (2R,3S,4R,5R)-3-<(1S)-1-<(benzyloxy)methyl>ethyl>-4,5-(isopropylidenedioxy)-2,3-dimethyltetrahydrofuran
• CAS No.: 129437-55-4
• Molecular Formula: C₁₉H₂₈O₄
• Molecular Weight: 320.429
• Mol file: 129437-55-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (2R,3S,4R,5R)-3-<(1S)-1-<(benzyloxy)methyl>ethyl>-4,5-(isopropylidenedioxy)-2,3-dimethyltetrahydrofuran 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: 70.0%

(βS,2R,3S,4R,5R)-4,5-(isopropylidenedioxy)-β,2,3-trimethyltetrahydrofuran-3-ethanol (129437-54-3,141660-87-9) + benzyl bromide (100-39-0) → (2R,3S,4R,5R)-3-<(1S)-1-<(benzyloxy)methyl>ethyl>-4,5-(isopropylidenedioxy)-2,3-dimethyltetrahydrofuran (129437-55-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

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

Reference yield:

(3aR,5S,6S,6aR)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-5,6-bis-(bis-ethylsulfanyl-methyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (129437-53-2,141660-86-8) → (2R,3S,4R,5R)-3-<(1S)-1-<(benzyloxy)methyl>ethyl>-4,5-(isopropylidenedioxy)-2,3-dimethyltetrahydrofuran (129437-55-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Raney nickel T-4 / ethanol / 4 h / Heating

2: 1.) NaH / 1.) DMF, r.t., 30 min, 2.) r.t., overnight

With Raney nickel T-4; sodium hydride; In ethanol;

DOI:10.1021/jo00040a014

Reference yield:

(3aR,5S,6R,6aR)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5,6-dicarbaldehyde (141585-51-5,141660-85-7) → (2R,3S,4R,5R)-3-<(1S)-1-<(benzyloxy)methyl>ethyl>-4,5-(isopropylidenedioxy)-2,3-dimethyltetrahydrofuran (129437-55-4)

Guidance literature:

Multi-step reaction with 3 steps

1: BF₃*OEt₂ / CH₂Cl₂ / 11.5 h / 0 °C

2: Raney nickel T-4 / ethanol / 4 h / Heating

3: 1.) NaH / 1.) DMF, r.t., 30 min, 2.) r.t., overnight

With Raney nickel T-4; boron trifluoride diethyl etherate; sodium hydride; In ethanol; dichloromethane;

DOI:10.1021/jo00040a014

upstream raw materials:

(βS,2R,3S,4R,5R)-4,5-(isopropylidenedioxy)-β,2,3-trimethyltetrahydrofuran-3-ethanol

benzyl bromide

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

(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

Downstream raw materials:

(2RS,3R,4S,5R)-4-<(1S)-1-<(benzyloxy)methyl>ethyl>-4,5-dimethyltetrahydrofuran-2,3-diol

(2R,3R,4S)-5-(benzyloxy)-3-(hydroxymethyl)-3,4-dimethylpentan-2-ol

(2S,3R,4R)-1-(benzyloxy)-4-(methoxymethoxy)-2,3-dimethyl-3-<(trimethylacetoxy)methyl>pentane

(-)-Acetomycin