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

Base Information

Chemical Name:(1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentanecarboxylic acid amide
CAS No.:189823-72-1
Molecular Formula:C₂₈H₃₁NO₄
Molecular Weight:445.558
Hs Code.:

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

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

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

There total 8 articles about (1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentanecarboxylic acid amide 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%

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

: 189823-72-1
(1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentanecarboxylic acid amide

Guidance literature:: With trimethylaluminum; ammonium chloride; In benzene; at 50 ℃; for 19h;
DOI:10.1021/jo970153d

Reference yield:

: 100-39-0
benzyl bromide

: 189823-72-1
(1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentanecarboxylic acid amide

Guidance literature:: Multi-step reaction with 5 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

5: 81 percent / NH₄Cl, Me₃Al / benzene / 19 h / 50 °C

With hydrogenchloride; sodium periodate; lithium borohydride; bromine; trimethylaluminum; sodium hydrogencarbonate; ammonium chloride; 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

: 189823-72-1
(1R,2S,3R,4R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-cyclopentanecarboxylic acid amide

Guidance literature:: Multi-step reaction with 7 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

7: 81 percent / NH₄Cl, Me₃Al / benzene / 19 h / 50 °C

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