(1S,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane

Base Information

• Chemical Name: (1S,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane
• CAS No.: 1054636-37-1
• Molecular Formula: C₇H₁₃N₃O₅
• Molecular Weight: 219.197
• Mol file: 1054636-37-1.mol

Synonyms:(1S,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane

Chemical Property of (1S,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane

There total 17 articles about (1S,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane 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: 97.0%

(1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-azido-4-hydroxycyclohexane-1,2,3-triyl triacetate (148347-73-3) → (1S,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane (1054636-37-1)

Guidance literature:

With ammonium hydroxide; In methanol; for 25h; Reflux;

DOI:10.1002/ejoc.201300804

Reference yield:

(1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane (83465-22-9) → (1S,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane (1054636-37-1)

Guidance literature:

With imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate; In methanol; at 20 ℃; for 12h;

DOI:10.1002/ejoc.201301874

Reference yield:

(3S,4R,5R)-5-methanesulfonyloxy-3,4-dihydroxy-1-cyclohexene-1-carboxylic acid ethyl ester (1476028-70-2) → (1S,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane (1054636-37-1)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium azide; acetic acid / dimethyl sulfoxide / 2 h / 85 °C

2: dmap; triethylamine / dichloromethane / 5 h / 20 °C

3: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -10 °C

4: dmap; triethylamine / ethyl acetate / 1 h / 0 °C

5: water; ruthenium trichloride; sodium periodate / acetonitrile / 4 h / 20 °C

6: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C

7: dmap; triethylamine / tetrahydrofuran / 1 h / 0 °C

8: ammonium hydroxide / methanol / 25 h / Reflux

With dmap; ruthenium trichloride; ammonium hydroxide; sodium periodate; sodium azide; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; acetic acid; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; acetonitrile;

DOI:10.1002/ejoc.201300804

upstream raw materials:

(1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-azido-4-hydroxycyclohexane-1,2,3-triyl triacetate

(1R)-(-)-1,2,3-tri-O-acetyl-(1,3/2,4,6)-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol

(1R)-(1,3/2,4)-2,3,4-triacetoxy-1-bromo-5-methylenecyclohexane

(3S,4R,5R)-5-methanesulfonyloxy-3,4-dihydroxy-1-cyclohexene-1-carboxylic acid ethyl ester

Downstream raw materials:

(1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane

(1S,2R,3S,4S,6S)-4-(acetoxymethyl)-4-hydroxy-6-[4-(4-nitrophenyl)-1H-1,2,3-triazol-1-yl]cyclohexane-1,2,3-triyl triacetate

(1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-[4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl]-4-hydroxycyclohexane-1,2,3-triyl triacetate

(1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-[4-(4-chlorophenyl)-1H-1,2,3-triazol-1-yl]-4-hydroxycyclohexane-1,2,3-triyl triacetate

Refernces

• 1、 Ji, Li,Zhou, Guo-Quan,Qian, Chao,Chen, Xin-Zhi. "Synthesis of 1,2,3-triazoles from azide-derivatised aminocyclitols by catalytic diazo transfer and CuAAC click chemistry". supporting information. p. 3622 - 3636. Retrieved 2014/06/23.
• 2、 Ogawa, Seiichiro,Sato, Koji,Miyamoto, Yasunobu. "Synthesis and Trehalose-inhibitory Activity of an Imino-linked Dicarba-&α,&α-trehalose and Analogues thereof". . p. 691 - 696. Retrieved 2007/10/02.