(1R,2S)-2-Benzyloxy-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

Base Information

• Chemical Name: (1R,2S)-2-Benzyloxy-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol
• CAS No.: 112699-64-6
• Molecular Formula: C₁₉H₂₈O₆
• Molecular Weight: 352.428

Synonyms:(1R,2S)-2-Benzyloxy-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

Chemical Property of (1R,2S)-2-Benzyloxy-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

Chemical Property:

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Technology Process of (1R,2S)-2-Benzyloxy-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

There total 2 articles about (1R,2S)-2-Benzyloxy-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol 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: 48.0%

benzyl chloride (100-44-7) + 1,2:5,6-di-O-isopropylidene-D-mannitol (1707-77-3) → (1R,2S)-2-Benzyloxy-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol (112699-64-6) + 3,4-di-O-benzyl-1,2:5,6-di-O-isopropylidene-D-mannitol (111476-62-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; Yields of byproduct given;

DOI:10.1021/jo961542v

Reference yield:

benzyl bromide (100-39-0) + 1,2:5,6-di-O-isopropylidene-D-mannitol (1707-77-3) → (1R,2S)-2-Benzyloxy-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol (112699-64-6)

Guidance literature:

With di(n-butyl)tin oxide; Yield given. Multistep reaction; 1) toluene, reflux, 2) DMF, 100 deg C;

DOI:10.1016/S0040-4039(00)96076-3

Reference yield: 86.0%

(1R,2S)-2-Benzyloxy-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol (112699-64-6) → (R)-2-Benzyloxy-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanone (189701-51-7)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -68 ℃; for 1h;

upstream raw materials:

benzyl bromide

1,2:5,6-di-O-isopropylidene-D-mannitol

benzyl chloride

Downstream raw materials:

Acetic acid (1R,2R)-2-benzyloxy-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester

(R)-2-Benzyloxy-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanone

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