(1R,2R,3S,4R,5R)-1-(azidomethyl)-2,3,4-tris(benzyloxy)-5-[(benzyloxy)methyl]cyclohexane-1-methanesulfonate

Base Information

Chemical Name:(1R,2R,3S,4R,5R)-1-(azidomethyl)-2,3,4-tris(benzyloxy)-5-[(benzyloxy)methyl]cyclohexane-1-methanesulfonate
CAS No.:639852-65-6
Molecular Formula:C₃₇H₄₁N₃O₇S
Molecular Weight:671.814
Hs Code.:

Synonyms:(1R,2R,3S,4R,5R)-1-(azidomethyl)-2,3,4-tris(benzyloxy)-5-[(benzyloxy)methyl]cyclohexane-1-methanesulfonate

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Chemical Property of (1R,2R,3S,4R,5R)-1-(azidomethyl)-2,3,4-tris(benzyloxy)-5-[(benzyloxy)methyl]cyclohexane-1-methanesulfonate

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Technology Process of (1R,2R,3S,4R,5R)-1-(azidomethyl)-2,3,4-tris(benzyloxy)-5-[(benzyloxy)methyl]cyclohexane-1-methanesulfonate

There total 4 articles about (1R,2R,3S,4R,5R)-1-(azidomethyl)-2,3,4-tris(benzyloxy)-5-[(benzyloxy)methyl]cyclohexane-1-methanesulfonate 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: 99.0%

: 124-63-0
methanesulfonyl chloride

: 639852-63-4
(1R,2R,3S,4R,5R)-1-azidomethyl-2,3,4-tris(benzyloxy)-5-[(benzyloxy)methyl]cyclohexan-1-ol

: 639852-65-6
(1R,2R,3S,4R,5R)-1-(azidomethyl)-2,3,4-tris(benzyloxy)-5-[(benzyloxy)methyl]cyclohexane-1-methanesulfonate

Guidance literature:: With 2,6-dimethylpyridine; dmap; at 0 ℃; for 7.5h;
DOI:10.1002/hlca.200390178

Reference yield:

: 124330-57-0
(2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-[(benzyloxy)methyl]cyclohexanone

: 639852-65-6
(1R,2R,3S,4R,5R)-1-(azidomethyl)-2,3,4-tris(benzyloxy)-5-[(benzyloxy)methyl]cyclohexane-1-methanesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: BuLi / hexane / 0 °C

1.2: 71 percent / tetrahydrofuran; hexane / 3 h

2.1: 61 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 3.67 h

3.1: 88 percent / NaN₃ / dimethylformamide / 20 h / 100 °C

4.1: 99 percent / 2,6-lutidine; DMAP / 7.5 h / 0 °C

With 2,6-dimethylpyridine; dmap; n-butyllithium; sodium azide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/hlca.200390178

Reference yield:

: 639852-45-2
(1S,2S,3R,4R)-1,2,3-tris(benzyloxy)-4-[(benzyloxy)methyl]-6-methylidenecyclohexane

: 639852-65-6
(1R,2R,3S,4R,5R)-1-(azidomethyl)-2,3,4-tris(benzyloxy)-5-[(benzyloxy)methyl]cyclohexane-1-methanesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1: 61 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 3.67 h

2: 88 percent / NaN₃ / dimethylformamide / 20 h / 100 °C

3: 99 percent / 2,6-lutidine; DMAP / 7.5 h / 0 °C

With 2,6-dimethylpyridine; dmap; sodium azide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/hlca.200390178