(1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentanecarboxylic acid methyl ester

Base Information

Chemical Name:(1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentanecarboxylic acid methyl ester
CAS No.:189823-68-5
Molecular Formula:C₂₉H₃₂O₅
Molecular Weight:460.57
Hs Code.:

Synonyms:(1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentanecarboxylic acid methyl ester

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Chemical Property of (1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentanecarboxylic acid methyl ester

Chemical Property:

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Technology Process of (1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentanecarboxylic acid methyl ester

There total 7 articles about (1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentanecarboxylic acid methyl ester 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: 81.0%

: 100-39-0
benzyl bromide

: 189823-66-3
(1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-hydroxymethyl-cyclopentanecarboxylic acid methyl ester

: 189823-68-5
(1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentanecarboxylic acid methyl ester

Guidance literature:: With silver(l) oxide; In benzene; at 0 - 20 ℃; for 23h;
DOI:10.1021/jo970153d

Reference yield:

: 100-39-0
benzyl bromide

: 189823-68-5
(1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 80 percent / Ag₂O, 3A MS / benzene / 23 h / 0 - 20 °C

2: 1.) O₃, 2.) LiBH₄, 3.) 12 N HCl, NaIO₄ / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 2.) THF, 0 deg C to room temperature, 20 h, 3.) THF, H₂O, room temperature, 2 h

3: 66 percent / Br₂, NaHCO₃ / H₂O / 1 h / Ambient temperature

4: 81 percent / Ag₂O, 3A MS / benzene / 23 h / 0 - 20 °C

With hydrogenchloride; sodium periodate; lithium borohydride; bromine; sodium hydrogencarbonate; ozone; silver(l) oxide; In water; benzene;
DOI:10.1021/jo970153d

Reference yield:

: 189823-58-3
(1R,2R,3R,4S)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester

: 189823-68-5
(1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 74 percent / OsO₄, NMO / acetone; H₂O / 13 h / 40 °C

2: 97 percent / DBU / diethyl ether / 24 h / Ambient temperature

3: 80 percent / Ag₂O, 3A MS / benzene / 23 h / 0 - 20 °C

4: 1.) O₃, 2.) LiBH₄, 3.) 12 N HCl, NaIO₄ / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 2.) THF, 0 deg C to room temperature, 20 h, 3.) THF, H₂O, room temperature, 2 h

5: 66 percent / Br₂, NaHCO₃ / H₂O / 1 h / Ambient temperature

6: 81 percent / Ag₂O, 3A MS / benzene / 23 h / 0 - 20 °C

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; bromine; sodium hydrogencarbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver(l) oxide; In diethyl ether; water; acetone; benzene;
DOI:10.1021/jo970153d