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

Base Information

• Chemical Name: (2S,3R,4R)-1-(benzyloxy)-4-(methoxymethoxy)-2,3-dimethyl-3-<(trimethylacetoxy)methyl>pentane
• CAS No.: 129437-56-5
• Molecular Formula: C₂₂H₃₆O₅
• Molecular Weight: 380.525
• Mol file: 129437-56-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (2S,3R,4R)-1-(benzyloxy)-4-(methoxymethoxy)-2,3-dimethyl-3-<(trimethylacetoxy)methyl>pentane 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: 96.0%

(2R,3R,4S)-5-(benzyloxy)-3,4-dimethyl-3-<(trimethylacetoxy)methyl>pentan-2-ol (129451-96-3) + chloromethyl methyl ether (107-30-2) → (2S,3R,4R)-1-(benzyloxy)-4-(methoxymethoxy)-2,3-dimethyl-3-<(trimethylacetoxy)methyl>pentane (129437-56-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 8h; Ambient temperature;

DOI:10.1021/jo00040a014

Reference yield:

(2RS,3R,4S,5R)-4-<(1S)-1-<(benzyloxy)methyl>ethyl>-4,5-dimethyltetrahydrofuran-2,3-diol (129451-94-1,141660-88-0,141660-92-6) → (2S,3R,4R)-1-(benzyloxy)-4-(methoxymethoxy)-2,3-dimethyl-3-<(trimethylacetoxy)methyl>pentane (129437-56-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaIO₄, 2.) NaBH₄ / 1.) MeOH, H₂O, r.t., 3 h, 2.) EtOH, r.t., 1 h

2: 80 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

3: 96 percent / (i-Pr)2EtN / CH₂Cl₂ / 8 h / Ambient temperature

With pyridine; sodium tetrahydroborate; sodium periodate; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo00040a014

Reference yield:

(2R,3S,4R,5R)-3-<(1S)-1-<(benzyloxy)methyl>ethyl>-4,5-(isopropylidenedioxy)-2,3-dimethyltetrahydrofuran (129437-55-4) → (2S,3R,4R)-1-(benzyloxy)-4-(methoxymethoxy)-2,3-dimethyl-3-<(trimethylacetoxy)methyl>pentane (129437-56-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / 20percent aq. oxalic acid / tetrahydrofuran / 72 h / 50 °C

2: 1.) NaIO₄, 2.) NaBH₄ / 1.) MeOH, H₂O, r.t., 3 h, 2.) EtOH, r.t., 1 h

3: 80 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; sodium tetrahydroborate; sodium periodate; oxalic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00040a014

upstream raw materials:

(2R,3R,4S)-5-(benzyloxy)-3,4-dimethyl-3-<(trimethylacetoxy)methyl>pentan-2-ol

chloromethyl methyl ether

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

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

Downstream raw materials:

(-)-Acetomycin