(1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol

Base Information

Chemical Name:(1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol
CAS No.:221371-29-5
Molecular Formula:C₂₈H₂₉N₃O₄
Molecular Weight:471.556
Hs Code.:

Synonyms:(1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol

Suppliers and Price of (1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol

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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 (1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol

There total 7 articles about (1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-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: 90.0%

: 221371-27-3
(1R,2S,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O,O-sulfonylcyclohex-5-ene-1,2,3,4-tetraol

: 221371-29-5
(1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol

Guidance literature:: With lithium azide; In N,N-dimethyl-formamide; at 80 ℃; for 3h;
DOI:10.1021/jo982024i

Reference yield: 77.0%

: 1169701-41-0
1,2-anhydro-3,4,6-tri-O-benzyl-5a-carba-β-D-lyxo-hex-5(5a)-enopyranose

: 221371-29-5
(1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol

Guidance literature:: With sodium azide; ammonium chloride; In tetrahydrofuran; methanol; water; at 0 ℃; for 14h;
DOI:10.1016/j.tetasy.2009.02.016

Reference yield:

: 100-39-0
benzyl bromide

: 221371-29-5
(1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / NaH, Bu₄NI / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) room temp., overnight

2: 70 percent / SOCl₂, pyridine / CH₂Cl₂ / 5.5 h / 0 °C

3: 85 percent / CF₃COOH, H₂O / CH₂Cl₂ / 24 h / Ambient temperature

4: 95 percent / SOCl₂, Et₃N / CH₂Cl₂ / 1 h / 0 °C

5: 90 percent / LiN₃ / dimethylformamide / 3 h / 80 °C

With pyridine; thionyl chloride; lithium azide; water; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo982024i