Acetic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-methoxy-3-nitromethyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-methoxy-3-nitromethyl-tetrahydro-pyran-3-yl ester
CAS No.:1053720-20-9
Molecular Formula:C₂₃H₂₇NO₈
Molecular Weight:445.469
Hs Code.:

Synonyms:

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Chemical Property of Acetic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-methoxy-3-nitromethyl-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-methoxy-3-nitromethyl-tetrahydro-pyran-3-yl ester

There total 8 articles about Acetic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-methoxy-3-nitromethyl-tetrahydro-pyran-3-yl ester 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:

: 28697-53-2
D-arabinopyranose

: 1053720-20-9
Acetic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-methoxy-3-nitromethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 9percent HCl / 15 h / Heating

2: p-toluenesulfonic acid monohydrate / dimethylformamide / 4 h / 25 °C

3: NaH / dimethylformamide / 1 h / 25 °C

4: 80percent acetic acid / H₂O / 8 h / 50 °C

5: 1.) dibutyltin oxide; 2.) CsF / 1.) toluene, reflux, 3 h; 2.) DMF, 25 deg C, 2 h

6: 1.) (COCl)2, DMSO; 2.) triethylamine / 1.) CH₂Cl₂, -40 deg C, 6 h; 2.) CH₂Cl₂, 25 deg C, 30 min

7: KF, 18-crown-6 / dimethylformamide / 0.5 h / 25 °C

8: p-toluenesulfonic acid monohydrate / 25 °C

With hydrogenchloride; potassium fluoride; oxalyl dichloride; 18-crown-6 ether; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; cesium fluoride; In water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89611-3

Reference yield:

: 149454-89-7
methyl 2,3-di-O-benzyl-β-D-arabinopyranoside

: 1053720-20-9
Acetic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-methoxy-3-nitromethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) (COCl)2, DMSO; 2.) triethylamine / 1.) CH₂Cl₂, -40 deg C, 6 h; 2.) CH₂Cl₂, 25 deg C, 30 min

2: KF, 18-crown-6 / dimethylformamide / 0.5 h / 25 °C

3: p-toluenesulfonic acid monohydrate / 25 °C

With potassium fluoride; oxalyl dichloride; 18-crown-6 ether; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89611-3

Reference yield:

: (3R,4R,5S,6R)-5-Benzyloxy-6-methoxy-tetrahydro-pyran-3,4-diol

: 1053720-20-9
Acetic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-methoxy-3-nitromethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) dibutyltin oxide; 2.) CsF / 1.) toluene, reflux, 3 h; 2.) DMF, 25 deg C, 2 h

2: 1.) (COCl)2, DMSO; 2.) triethylamine / 1.) CH₂Cl₂, -40 deg C, 6 h; 2.) CH₂Cl₂, 25 deg C, 30 min

3: KF, 18-crown-6 / dimethylformamide / 0.5 h / 25 °C

4: p-toluenesulfonic acid monohydrate / 25 °C

With potassium fluoride; oxalyl dichloride; 18-crown-6 ether; di(n-butyl)tin oxide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; cesium fluoride; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89611-3