(+)-(1R,2S,5S,6R)-5-azido-3-chloro-2-hydroxy-6-(1',3',4',5'-tetra-O-acetyl-2',6'-anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'-C-yl)cyclohex-3-en-7-yl acetate

Base Information

Chemical Name:(+)-(1R,2S,5S,6R)-5-azido-3-chloro-2-hydroxy-6-(1',3',4',5'-tetra-O-acetyl-2',6'-anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'-C-yl)cyclohex-3-en-7-yl acetate
CAS No.:288574-21-0
Molecular Formula:C₂₃H₃₀ClN₃O₁₂
Molecular Weight:575.957
Hs Code.:

Synonyms:(+)-(1R,2S,5S,6R)-5-azido-3-chloro-2-hydroxy-6-(1',3',4',5'-tetra-O-acetyl-2',6'-anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'-C-yl)cyclohex-3-en-7-yl acetate

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Chemical Property of (+)-(1R,2S,5S,6R)-5-azido-3-chloro-2-hydroxy-6-(1',3',4',5'-tetra-O-acetyl-2',6'-anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'-C-yl)cyclohex-3-en-7-yl acetate

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Technology Process of (+)-(1R,2S,5S,6R)-5-azido-3-chloro-2-hydroxy-6-(1',3',4',5'-tetra-O-acetyl-2',6'-anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'-C-yl)cyclohex-3-en-7-yl acetate

There total 7 articles about (+)-(1R,2S,5S,6R)-5-azido-3-chloro-2-hydroxy-6-(1',3',4',5'-tetra-O-acetyl-2',6'-anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'-C-yl)cyclohex-3-en-7-yl acetate 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%

: 288574-20-9
(+)-(1R,2S,5R,6S)-5-bromo-3-chloro-2-hydroxy-6-(1',3',4',5'-tetra-O-acetyl-2',6'-anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'-C-yl)cyclohex-3-en-7-yl acetate

: 288574-21-0
(+)-(1R,2S,5S,6R)-5-azido-3-chloro-2-hydroxy-6-(1',3',4',5'-tetra-O-acetyl-2',6'-anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'-C-yl)cyclohex-3-en-7-yl acetate

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 60 ℃; for 0.25h;
DOI:10.1021/jo991952u

Reference yield:

: 134160-51-3
(-)-(1S,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7-oxabicyclo<2.2.1>heptan-2-one

: 288574-21-0
(+)-(1R,2S,5S,6R)-5-azido-3-chloro-2-hydroxy-6-(1',3',4',5'-tetra-O-acetyl-2',6'-anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'-C-yl)cyclohex-3-en-7-yl acetate

Guidance literature:: Multi-step reaction with 6 steps

1: 56 percent / azobis(isobutyronitrile); Ph₃SnH / benzene / 1 h / Heating

2: 79 percent / NaBH₄ / tetrahydrofuran; methanol / 0.08 h / 0 °C

3: 94 percent / m-chloroperbenzoic acid; m-chlorobenzoic acid / CH₂Cl₂ / -78 - 20 °C

4: 92 percent / pyridine; 4-(dimethylamino)pyridine / 7 h / 20 °C

5: 72 percent / BBr₃ / CH₂Cl₂ / 0.25 h / 0 °C

6: 98 percent / sodium azide / dimethylformamide / 0.25 h / 60 °C

With pyridine; dmap; sodium tetrahydroborate; sodium azide; 2,2'-azobis(isobutyronitrile); triphenylstannane; boron tribromide; 3-chloro-benzenecarboperoxoic acid; 3-chlorobenzoate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: mannosidation / 2: Reduction / 3: Elimination / 4: Acetylation / 5: Ring cleavage / 6: Substitution;
DOI:10.1021/jo991952u

Reference yield:

: 222317-37-5
(+)-(1S,2R,3S,4R)-6-chloro-3-endo-(1',3',4',5'-tetra-O-acetyl-2',6'-anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'-C-yl)-7-oxabicyclo[2.2.1]hept-5-en-2-endo-ol

: 288574-21-0
(+)-(1R,2S,5S,6R)-5-azido-3-chloro-2-hydroxy-6-(1',3',4',5'-tetra-O-acetyl-2',6'-anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'-C-yl)cyclohex-3-en-7-yl acetate

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / pyridine; 4-(dimethylamino)pyridine / 7 h / 20 °C

2: 72 percent / BBr₃ / CH₂Cl₂ / 0.25 h / 0 °C

3: 98 percent / sodium azide / dimethylformamide / 0.25 h / 60 °C

With pyridine; dmap; sodium azide; boron tribromide; In dichloromethane; N,N-dimethyl-formamide; 1: Acetylation / 2: Ring cleavage / 3: Substitution;
DOI:10.1021/jo991952u