(1S,2S,3R,4S)-1-(2',2',2'-trichloromethylcarbonylamino)-2,3,4-trihydroxycyclohexane

Base Information

Chemical Name:(1S,2S,3R,4S)-1-(2',2',2'-trichloromethylcarbonylamino)-2,3,4-trihydroxycyclohexane
CAS No.:1299472-59-5
Molecular Formula:C₈H₁₂Cl₃NO₄
Molecular Weight:292.547
Hs Code.:

Synonyms:(1S,2S,3R,4S)-1-(2',2',2'-trichloromethylcarbonylamino)-2,3,4-trihydroxycyclohexane

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Chemical Property of (1S,2S,3R,4S)-1-(2',2',2'-trichloromethylcarbonylamino)-2,3,4-trihydroxycyclohexane

Chemical Property:

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Technology Process of (1S,2S,3R,4S)-1-(2',2',2'-trichloromethylcarbonylamino)-2,3,4-trihydroxycyclohexane

There total 10 articles about (1S,2S,3R,4S)-1-(2',2',2'-trichloromethylcarbonylamino)-2,3,4-trihydroxycyclohexane 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: 87.0%

: 1299472-58-4
2',2',2'-trichloro-N-[(1S,2S,3S,6R)-2-hydroxy-7-oxabicyclo[4.1.0]hept-3-yl]acetamide

: 1299472-59-5
(1S,2S,3R,4S)-1-(2',2',2'-trichloromethylcarbonylamino)-2,3,4-trihydroxycyclohexane

Guidance literature:: With sulfuric acid; In 1,4-dioxane; at 20 ℃; for 8h;
DOI:10.1039/c0ob00619j

Reference yield:

: 821-41-0
5-Hexen-1-ol

: 1299472-59-5
(1S,2S,3R,4S)-1-(2',2',2'-trichloromethylcarbonylamino)-2,3,4-trihydroxycyclohexane

Guidance literature:: Multi-step reaction with 10 steps

1.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 20 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / diethyl ether; hexane / -78 - 20 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

4.1: di-μ-chlorobis[(η(5)-(S)-(pR)-2-(2'-(4'-(1-methylethyl))oxazolinyl)cyclopentadienyl, 1-C, 3'-N)(η(4)-tetraphenylcyclobutadiene)cobalt]dipalladium / dichloromethane / 72 h / 45 °C / Inert atmosphere

5.1: Grubbs catalyst first generation / dichloromethane / 65 °C

6.1: N-iodo-succinimide / chloroform / 18 h / Inert atmosphere

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 12 h / Reflux; Inert atmosphere

8.1: hydrogenchloride; water / methanol / 1 h / 20 °C

9.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C

10.1: sulfuric acid / 1,4-dioxane / 8 h / 20 °C

With Grubbs catalyst first generation; hydrogenchloride; N-iodo-succinimide; oxalyl dichloride; di-μ-chlorobis[(η(5)-(S)-(pR)-2-(2'-(4'-(1-methylethyl))oxazolinyl)cyclopentadienyl, 1-C, 3'-N)(η(4)-tetraphenylcyclobutadiene)cobalt]dipalladium; sulfuric acid; water; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; In 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; chloroform; toluene; 1.1: Swern oxidation / 1.2: Horner-Wadsworth-Emmons olefination / 4.1: Overman rearrangement;
DOI:10.1039/c0ob00619j

Reference yield:

: 1299472-54-0
C₈H₉Cl₃INO

: 1299472-59-5
(1S,2S,3R,4S)-1-(2',2',2'-trichloromethylcarbonylamino)-2,3,4-trihydroxycyclohexane

Guidance literature:: Multi-step reaction with 4 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 12 h / Reflux; Inert atmosphere

2: hydrogenchloride; water / methanol / 1 h / 20 °C

3: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C

4: sulfuric acid / 1,4-dioxane / 8 h / 20 °C

With hydrogenchloride; sulfuric acid; water; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In 1,4-dioxane; methanol; dichloromethane; toluene;
DOI:10.1039/c0ob00619j