(4S,5S,1'S)-5-benzyloxymethyl-2,2-dimethyl-4(1'-benzyloxypentan-1'-yl)-1,3-dioxolan

Base Information

• Chemical Name: (4S,5S,1'S)-5-benzyloxymethyl-2,2-dimethyl-4(1'-benzyloxypentan-1'-yl)-1,3-dioxolan
• CAS No.: 111828-40-1
• Molecular Formula: C₂₅H₃₄O₄
• Molecular Weight: 398.543
• Mol file: 111828-40-1.mol

Synonyms:(4S,5S,1'S)-5-benzyloxymethyl-2,2-dimethyl-4(1'-benzyloxypentan-1'-yl)-1,3-dioxolan

Chemical Property of (4S,5S,1'S)-5-benzyloxymethyl-2,2-dimethyl-4(1'-benzyloxypentan-1'-yl)-1,3-dioxolan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S,1'S)-5-benzyloxymethyl-2,2-dimethyl-4(1'-benzyloxypentan-1'-yl)-1,3-dioxolan

There total 3 articles about (4S,5S,1'S)-5-benzyloxymethyl-2,2-dimethyl-4(1'-benzyloxypentan-1'-yl)-1,3-dioxolan 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: 85.0%

benzyl bromide (100-39-0) + (2S,3S)-1-benzyloxy-2,3-isopropylidenedioxy-4-(S)-octanol (111828-39-8) → (4S,5S,1'S)-5-benzyloxymethyl-2,2-dimethyl-4(1'-benzyloxypentan-1'-yl)-1,3-dioxolan (111828-40-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -40 - 20 ℃; for 2.5h;

Reference yield: 85.0%

benzyl bromide (100-39-0) + (2S,3S)-1-benzyloxy-2,3-isopropylidenedioxy-4-(R)-octanol (111901-78-1) → (4S,5S,1'S)-5-benzyloxymethyl-2,2-dimethyl-4(1'-benzyloxypentan-1'-yl)-1,3-dioxolan (111828-40-1)

Guidance literature:

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

DOI:10.1016/S0040-4039(00)96267-1

Reference yield:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) → (4S,5S,1'S)-5-benzyloxymethyl-2,2-dimethyl-4(1'-benzyloxypentan-1'-yl)-1,3-dioxolan (111828-40-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / ZnBr₂ / hexane; tetrahydrofuran / 0.5 h / -78 - 20 °C

2: 85 percent / sodium hydride / dimethylformamide / 2.5 h / -40 - 20 °C

With sodium hydride; zinc dibromide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

upstream raw materials:

benzyl bromide

(2S,3S)-1-benzyloxy-2,3-isopropylidenedioxy-4-(R)-octanol

(2S,3S)-1-benzyloxy-2,3-isopropylidenedioxy-4-(S)-octanol

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

Downstream raw materials:

1,4-di-O-benzyl-octane-1,2,3,4-tetrol