(1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxymethyl-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane

Base Information

Chemical Name:(1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxymethyl-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane
CAS No.:199122-41-3
Molecular Formula:C₁₈H₂₄O₄
Molecular Weight:304.386
Hs Code.:

Synonyms:(1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxymethyl-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane

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Chemical Property of (1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxymethyl-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane

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Technology Process of (1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxymethyl-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane

There total 7 articles about (1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxymethyl-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane 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: 90.0%

: 199122-38-8
(1R,3R,4S,5S)-1-<(benzyloxy)methyl>-3,4-(isopropylidenedioxy)-2-C-methylenebicyclo<3.1.0>hexane

: 199122-41-3
(1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxymethyl-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane

: (1S,2R,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxymethyl-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane

Guidance literature:: With sodium perborate; borane-THF; In tetrahydrofuran; at 0 - 20 ℃; for 16h;
DOI:10.1021/jo990010m

Reference yield:

: 156126-13-5
(1aR,1bR,4aS,5S,5aS)-1a-Benzyloxymethyl-3,3-dimethyl-hexahydro-2,4-dioxa-cyclopropa[a]pentalen-5-ol

: 199122-41-3
(1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxymethyl-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 4 steps

1: 57 percent / p-TsOH*H₂O / 2 h / Heating

2: 100 percent / TPAP, NMO, 4A MS / CH₂Cl₂ / 0.67 h / Ambient temperature

3: 90 percent / n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

4: 90 percent / BH₃*THF, NaBO₃*H₂O / tetrahydrofuran / 16 h / 0 - 20 °C

With sodium perborate; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo990010m

Reference yield:

: 199122-34-4
(1R,3R,4S,5S)-1-<(benzyloxy)methyl>-3,4-(isopropylidenedioxy)-2-oxo-bicyclo<3.1.0>hexane

: 199122-41-3
(1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxymethyl-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

2: 90 percent / BH₃*THF, NaBO₃*H₂O / tetrahydrofuran / 16 h / 0 - 20 °C

With sodium perborate; n-butyllithium; borane-THF; In tetrahydrofuran; hexane;
DOI:10.1021/jo990010m