(1S,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene

Base Information

Chemical Name:(1S,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene
CAS No.:134680-57-2
Molecular Formula:C₂₈H₂₉NO₅
Molecular Weight:459.542
Hs Code.:

Synonyms:(1S,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene

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Chemical Property of (1S,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene

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Technology Process of (1S,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene

There total 4 articles about (1S,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene 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: 15.0%

: 128184-65-6,134680-70-9,134731-71-8,139402-97-4,139402-98-5
2,3,4-tri-O-benzyl-6,7-dideoxy-D-galacto-hept-6-enose-oxime

: 134680-58-3
(3aR,4R,5S,6R,7S)-5,6,7-Tris-benzyloxy-3,3a,4,5,6,7-hexahydro-benzo[c]isoxazol-4-ol

: 134680-57-2
(1S,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene

Guidance literature:: With sodium hypochlorite; In toluene; at 100 ℃; for 0.5h;
DOI:10.1016/0008-6215(91)89017-A

Reference yield:

: 4356-80-3,34212-64-1,40653-32-5,53008-65-4,68027-27-0,73111-53-2,128184-63-4,138794-99-7,55094-38-7,641635-63-4
methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside

: 134680-57-2
(1S,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 1) oxalyl chloride, DMSO, 2) NET₃ / 1) CH₂Cl₂, -78 deg C, 15 min, 2a) -78 deg C, 15 min, 2b) -78 to -40 deg C

2: 91 percent / benzene / 0.17 h / 25 °C

3: 1) Ac₂O, conc. H₂SO₄, 2) NaOMe / 1) 0 deg C, 10 min, 2a) MeOH, 0 deg c, 10 min, 2b) 25 deg C, 0.5h

4: 100 percent / H₂NNH₂*HCl, pyridine / 3 h / 25 °C

5: 15 percent / 5percent aq. NaOCl / toluene / 0.5 h / 100 °C

With pyridine; sodium hypochlorite; oxalyl dichloride; hydrazine hydrochloride; sulfuric acid; sodium methylate; acetic anhydride; dimethyl sulfoxide; triethylamine; In toluene; benzene;
DOI:10.1016/0008-6215(91)89017-A

Reference yield:

: 139285-93-1
(2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal

: 134680-57-2
(1S,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / H₂NNH₂*HCl, pyridine / 3 h / 25 °C

2: 15 percent / 5percent aq. NaOCl / toluene / 0.5 h / 100 °C

With pyridine; sodium hypochlorite; hydrazine hydrochloride; In toluene;
DOI:10.1016/0008-6215(91)89017-A