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

Base Information

Chemical Name:(1R,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane
CAS No.:1476028-79-1
Molecular Formula:C₇H₁₃N₃O₅
Molecular Weight:219.197
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

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

There total 12 articles about (1R,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: 96.0%

: 694527-30-5
1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4-tri-O-acetyl-5-azido-1,2,3,4-cyclohexanetetrol

: 1476028-79-1
(1R,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane

Guidance literature:: With ammonium hydroxide; In methanol; for 25h; Reflux;
DOI:10.1002/ejoc.201300804

Reference yield:

: 1476028-70-2
(3S,4R,5R)-5-methanesulfonyloxy-3,4-dihydroxy-1-cyclohexene-1-carboxylic acid ethyl ester

: 1476028-79-1
(1R,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane

Guidance literature:: Multi-step reaction with 8 steps

1: sodium azide / ethanol / 3 h / Reflux

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; triethylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1002/ejoc.201300804

Reference yield:

: 1476028-72-4
(3S,4R,5R)-5-azido-3,4-dihydroxy-1-cyclohexene-1-carboxylic acid ethyl ester

: 1476028-79-1
(1R,2S,3R,4S,5S)-1-azido-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane

Guidance literature:: Multi-step reaction with 7 steps

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

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

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

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

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

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

7: ammonium hydroxide / methanol / 25 h / Reflux

With dmap; ruthenium trichloride; ammonium hydroxide; sodium periodate; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1002/ejoc.201300804