(R)-2-(benzyloxy)-1-{(4R,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi-(1,3-dioxolan)]-5-yl}ethanol

Base Information

Chemical Name:(R)-2-(benzyloxy)-1-{(4R,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi-(1,3-dioxolan)]-5-yl}ethanol
CAS No.:1605289-85-7
Molecular Formula:C₁₉H₂₈O₆
Molecular Weight:352.428
Hs Code.:

Synonyms:(R)-2-(benzyloxy)-1-{(4R,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi-(1,3-dioxolan)]-5-yl}ethanol

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Chemical Property of (R)-2-(benzyloxy)-1-{(4R,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi-(1,3-dioxolan)]-5-yl}ethanol

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Technology Process of (R)-2-(benzyloxy)-1-{(4R,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi-(1,3-dioxolan)]-5-yl}ethanol

There total 3 articles about (R)-2-(benzyloxy)-1-{(4R,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi-(1,3-dioxolan)]-5-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: 73.0%

: 100-39-0
benzyl bromide

: 38145-93-6
1,2:3,4-di-O-isopropylidene-D-mannitol

: 1605289-85-7
(R)-2-(benzyloxy)-1-{(4R,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi-(1,3-dioxolan)]-5-yl}ethanol

Guidance literature:: With di(n-butyl)tin oxide; In toluene; regioselective reaction;
DOI:10.1016/j.tetlet.2017.04.049

Reference yield:

: 69-65-8
mannitol

: 1605289-85-7
(R)-2-(benzyloxy)-1-{(4R,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi-(1,3-dioxolan)]-5-yl}ethanol

Guidance literature:: Multi-step reaction with 3 steps

1.1: camphorsulfonic acid (CSA) / N,N-dimethyl-formamide / 70 °C

2.1: sulfuric acid; silica gel / methanol

3.1: di(n-butyl)tin oxide / toluene / 16 h / Reflux; Dean-Stark

3.2: 12 h

With sulfuric acid; silica gel; di(n-butyl)tin oxide; In methanol; N,N-dimethyl-formamide; toluene;
DOI:10.1002/ejoc.201301782

Reference yield:

: 3969-59-3
mannitol triacetonide

: 1605289-85-7
(R)-2-(benzyloxy)-1-{(4R,4'R,5R)-2,2,2',2'-tetramethyl-[4,4'-bi-(1,3-dioxolan)]-5-yl}ethanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: sulfuric acid; silica gel / methanol

2.1: di(n-butyl)tin oxide / toluene / 16 h / Reflux; Dean-Stark

2.2: 12 h

With sulfuric acid; silica gel; di(n-butyl)tin oxide; In methanol; toluene;
DOI:10.1002/ejoc.201301782