(1R,3S,4S,5S,6R)-7-aza-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-bicyclo<4,4,0>-decane

Base Information

Chemical Name:(1R,3S,4S,5S,6R)-7-aza-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-bicyclo<4,4,0>-decane
CAS No.:91652-64-1
Molecular Formula:C₁₈H₂₅NO₄
Molecular Weight:319.401
Hs Code.:

Synonyms:(1R,3S,4S,5S,6R)-7-aza-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-bicyclo<4,4,0>-decane

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Chemical Property of (1R,3S,4S,5S,6R)-7-aza-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-bicyclo<4,4,0>-decane

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Technology Process of (1R,3S,4S,5S,6R)-7-aza-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-bicyclo<4,4,0>-decane

There total 27 articles about (1R,3S,4S,5S,6R)-7-aza-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-bicyclo<4,4,0>-decane 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: 89.0%

: 140428-36-0
(1R,3S,4S,5S,6R)-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-7-azabicyclo<4.4.0>decan-8-one

: 91652-64-1
(1R,3S,4S,5S,6R)-7-aza-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-bicyclo<4,4,0>-decane

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; Ambient temperature;
DOI:10.1246/bcsj.65.567

Reference yield: 61.0%

: 114894-84-7
benzyl 4-benzyloxycarbonylamino-4,6,7-trideoxy-6-ene-2,3-O-isopropylidene-α-D-manno-octadialdopyranoside

: 91652-64-1
(1R,3S,4S,5S,6R)-7-aza-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-bicyclo<4,4,0>-decane

: 114894-86-9
(3aS,4S,5aR,9aR,9bS)-4-Benzyloxy-2,2,9-trimethyl-octahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-b]pyridine

Guidance literature:: With hydrogen; palladium; In methanol; for 48h;
DOI:10.1016/S0040-4020(01)86850-2

Reference yield:

: 15548-45-5
(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

: 91652-64-1
(1R,3S,4S,5S,6R)-7-aza-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-bicyclo<4,4,0>-decane

Guidance literature:: Multi-step reaction with 14 steps

1: 75 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 94.3 percent / 2-naphthalenesulfonic acid / acetone / 8 h / Ambient temperature

3: 94 percent / triethylamine / tetrahydrofuran / Ambient temperature

4: 1.) Na / 1.) toluene, reflux, 2.) toluene, reflux, overnight

5: 70 percent / DMSO, NaCl / H₂O / 15 h / 145 °C

6: 1 g / 1 M aq. KOH / methanol / Ambient temperature

7: 96 percent / diethyl ether

8: 95 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / Ambient temperature

9: 97 percent / NaBH₄ / ethanol / 0.5 h / Ambient temperature

10: 88 percent / pyridine / CH₂Cl₂ / 15 h / -20 °C

11: 65 percent / NaN₃ / dimethylformamide / 15 h / Ambient temperature

12: H₂ / Pd / methanol / 6 h / Ambient temperature

13: toluene / 1 h / Heating

14: 89 percent / LAH / tetrahydrofuran / Ambient temperature

With pyridine; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; naphthalene-2-sulfonate; hydrogen; sodium; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; sodium chloride; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1246/bcsj.65.567