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

Base Information

• Chemical Name: (2R,3R,4S)-5-(benzyloxy)-3-(hydroxymethyl)-3,4-dimethylpentan-2-ol
• CAS No.: 129451-95-2
• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.354
• Mol file: 129451-95-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (2R,3R,4S)-5-(benzyloxy)-3-(hydroxymethyl)-3,4-dimethylpentan-2-ol 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:

(βS,2R,3S,4R,5R)-4,5-(isopropylidenedioxy)-β,2,3-trimethyltetrahydrofuran-3-ethanol (129437-54-3,141660-87-9) → (2R,3R,4S)-5-(benzyloxy)-3-(hydroxymethyl)-3,4-dimethylpentan-2-ol (129451-95-2)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 79 percent / 20percent aq. oxalic acid / tetrahydrofuran / 72 h / 50 °C

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

With sodium tetrahydroborate; sodium periodate; oxalic acid; sodium hydride; In tetrahydrofuran;

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) → (2R,3R,4S)-5-(benzyloxy)-3-(hydroxymethyl)-3,4-dimethylpentan-2-ol (129451-95-2)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1021/jo00040a014

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,3R,4S)-5-(benzyloxy)-3-(hydroxymethyl)-3,4-dimethylpentan-2-ol (129451-95-2)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 79 percent / 20percent aq. oxalic acid / tetrahydrofuran / 72 h / 50 °C

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

With sodium tetrahydroborate; sodium periodate; Raney nickel T-4; oxalic acid; sodium hydride; In tetrahydrofuran; ethanol;

DOI:10.1021/jo00040a014

upstream raw materials:

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

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

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

(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

Downstream raw materials:

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

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

(-)-Acetomycin