(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-pyran

Base Information

Chemical Name:(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-pyran
CAS No.:149454-92-2
Molecular Formula:C₂₁H₂₅NO₆
Molecular Weight:387.433
Hs Code.:

Synonyms:(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-pyran

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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 (2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-pyran

Chemical Property:

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Technology Process of (2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-pyran

There total 12 articles about (2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-pyran 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:

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

: 149454-92-2
(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-pyran

Guidance literature:: With sodium tetrahydroborate; In ethanol; at 25 ℃; for 1h; Yield given;
DOI:10.1016/S0040-4020(01)89611-3

Reference yield:

: 149454-88-6
methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-arabinopyranoside

: 149454-92-2
(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 6 steps

1: 80percent acetic acid / H₂O / 8 h / 50 °C

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

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

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

5: p-toluenesulfonic acid monohydrate / 25 °C

6: NaBH₄ / ethanol / 1 h / 25 °C

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

Reference yield:

: 149454-91-1
(3R,4S,5S,6R)-4,5-Bis-benzyloxy-6-methoxy-3-nitromethyl-tetrahydro-pyran-3-ol

: 149454-92-2
(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-methoxy-5-nitromethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: p-toluenesulfonic acid monohydrate / 25 °C

2: NaBH₄ / ethanol / 1 h / 25 °C

With sodium tetrahydroborate; toluene-4-sulfonic acid; In ethanol;
DOI:10.1016/S0040-4020(01)89611-3