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

Base Information

• Chemical Name: (1S,2R,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane
• CAS No.: 199122-31-1
• Molecular Formula: C₁₇H₂₂O₄
• Molecular Weight: 290.359

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

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

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

There total 4 articles about (1S,2R,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxy-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: 57.0%

(1aR,1bR,4aS,5S,5aS)-1a-Benzyloxymethyl-3,3-dimethyl-hexahydro-2,4-dioxa-cyclopropa[a]pentalen-5-ol (156126-13-5) → (1S,2R,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane (199122-31-1)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 50 ℃; for 2h;

DOI:10.1016/0040-4039(96)00289-4

Reference yield: 57.0%

acetone (67-64-1) + (1aR,1bR,4aS,5S,5aS)-1a-Benzyloxymethyl-3,3-dimethyl-hexahydro-2,4-dioxa-cyclopropa[a]pentalen-5-ol (156126-13-5) → (1S,2R,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane (199122-31-1)

Guidance literature:

With toluene-4-sulfonic acid; at 50 ℃; for 2h;

DOI:10.1080/07328319708006132

Reference yield:

(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol (89291-76-9) → (1S,2R,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane (199122-31-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Et₂Zn / tetrahydrofuran / Ambient temperature

2: 57 percent / p-TsOH / 2 h / 50 °C

With diethylzinc; toluene-4-sulfonic acid; In tetrahydrofuran;

DOI:10.1080/07328319708006132

upstream raw materials:

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

acetone

(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol

(3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one

Downstream raw materials:

1-[(1S,2R,3R,4S,5S)-4,5-Bis-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-bicyclo[3.1.0]hex-2-yl]-3-((Z)-3-ethoxy-acryloyl)-isourea

(1S,2S,3R,4R,5S)-4-(2-Amino-6-chloro-purin-9-yl)-1,2-bis-benzyloxymethyl-bicyclo[3.1.0]hexan-3-ol

9-((1S,2S,4S,5S)-4,5-Bis-benzyloxymethyl-bicyclo[3.1.0]hex-2-yl)-6-chloro-9H-purin-2-ylamine

dithiocarbonic acid O-[4-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-1,2-bis-benzyloxymethyl-bicyclo[3.1.0]hex-3-yl] ester S-methyl ester

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