(2S,3S,4R)-3,5-O-dibenzyloxy-1,2,4-O-tri-tert-butyldimethylsilyloxypentane

Base Information

Chemical Name:(2S,3S,4R)-3,5-O-dibenzyloxy-1,2,4-O-tri-tert-butyldimethylsilyloxypentane
CAS No.:765942-29-8
Molecular Formula:C₃₇H₆₆O₅Si₃
Molecular Weight:675.185
Hs Code.:

Synonyms:(2S,3S,4R)-3,5-O-dibenzyloxy-1,2,4-O-tri-tert-butyldimethylsilyloxypentane

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Chemical Property of (2S,3S,4R)-3,5-O-dibenzyloxy-1,2,4-O-tri-tert-butyldimethylsilyloxypentane

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Technology Process of (2S,3S,4R)-3,5-O-dibenzyloxy-1,2,4-O-tri-tert-butyldimethylsilyloxypentane

There total 8 articles about (2S,3S,4R)-3,5-O-dibenzyloxy-1,2,4-O-tri-tert-butyldimethylsilyloxypentane 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: 97.6%

: 69739-34-0
t-butyldimethylsiyl triflate

: 16054-78-7
(2S,3S,4R)-3,5-O-dibenzyloxy-1,2,4-pentanetriol

: 765942-29-8
(2S,3S,4R)-3,5-O-dibenzyloxy-1,2,4-O-tri-tert-butyldimethylsilyloxypentane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/jo049033d

Reference yield:

: 37077-81-9
1,2-isopropylidene-α-D-ribofuranose

: 765942-29-8
(2S,3S,4R)-3,5-O-dibenzyloxy-1,2,4-O-tri-tert-butyldimethylsilyloxypentane

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: 91.5 percent / tetrahydrofuran / 2 h / Heating

2.1: aq. AcOH / 3.5 h / Heating

2.2: 91.8 percent / NaBH₄ / methanol / 20 °C

3.1: 97.6 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; sodium hydride; acetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo049033d

Reference yield:

: 100-39-0
benzyl bromide

: 765942-29-8
(2S,3S,4R)-3,5-O-dibenzyloxy-1,2,4-O-tri-tert-butyldimethylsilyloxypentane

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: 91.5 percent / tetrahydrofuran / 2 h / Heating

2.1: aq. AcOH / 3.5 h / Heating

2.2: 91.8 percent / NaBH₄ / methanol / 20 °C

3.1: 97.6 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; sodium hydride; acetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo049033d