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

Base Information

Chemical Name:(1S,2R,3S,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)-2-O-methanesulfonylcyclohex-5-ene-2,3,4-triol
CAS No.:221371-37-5
Molecular Formula:C₂₉H₃₁N₃O₆S
Molecular Weight:549.648
Hs Code.:

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

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Chemical Property of (1S,2R,3S,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)-2-O-methanesulfonylcyclohex-5-ene-2,3,4-triol

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

There total 7 articles about (1S,2R,3S,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)-2-O-methanesulfonylcyclohex-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: 98.0%

: 124-63-0
methanesulfonyl chloride

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

: 221371-37-5
(1S,2R,3S,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)-2-O-methanesulfonylcyclohex-5-ene-2,3,4-triol

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/jo982024i

Reference yield:

: 100-39-0
benzyl bromide

: 221371-37-5
(1S,2R,3S,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)-2-O-methanesulfonylcyclohex-5-ene-2,3,4-triol

Guidance literature:: Multi-step reaction with 6 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

6: 98 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °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

Reference yield:

: 183268-55-5
(1R,2R,3S,4S,5S)-3-O-benzyl-5-((benzyloxy)methyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol

: 221371-37-5
(1S,2R,3S,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)-2-O-methanesulfonylcyclohex-5-ene-2,3,4-triol

Guidance literature:: Multi-step reaction with 6 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

6: 98 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °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