(1S,2S,3R,4S)-1-aminocyclohexane-2,3,4-triol

Base Information

Chemical Name:(1S,2S,3R,4S)-1-aminocyclohexane-2,3,4-triol
CAS No.:1300575-56-7
Molecular Formula:C₆H₁₃NO₃
Molecular Weight:147.174
Hs Code.:

Synonyms:(1S,2S,3R,4S)-1-aminocyclohexane-2,3,4-triol

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Chemical Property of (1S,2S,3R,4S)-1-aminocyclohexane-2,3,4-triol

Chemical Property:

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Technology Process of (1S,2S,3R,4S)-1-aminocyclohexane-2,3,4-triol

There total 11 articles about (1S,2S,3R,4S)-1-aminocyclohexane-2,3,4-triol 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: 98.0%

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

: 1300575-56-7,321164-63-0
(1S,2S,3R,4S)-1-aminocyclohexane-2,3,4-triol

Guidance literature:: With water; sodium hydroxide; In methanol; at 20 ℃; for 12h;
DOI:10.1039/c0ob00619j

Reference yield:

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

: 1300575-56-7,321164-63-0
(1S,2S,3R,4S)-1-aminocyclohexane-2,3,4-triol

Guidance literature:: Multi-step reaction with 11 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

11.1: water; sodium hydroxide / methanol / 12 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; sodium hydroxide; 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:

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

: 1300575-56-7,321164-63-0
(1S,2S,3R,4S)-1-aminocyclohexane-2,3,4-triol

Guidance literature:: Multi-step reaction with 2 steps

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

2: water; sodium hydroxide / methanol / 12 h / 20 °C

With sulfuric acid; water; sodium hydroxide; In 1,4-dioxane; methanol;
DOI:10.1039/c0ob00619j