<4aR-(4aα,5β,6β,7β,7aα)>-2-<(2,3,4,6-Tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-7-(benzyloxy)-4,4a,5,6,7,7a-hexahydro-4a,5,6,7a-tetrahydroxycyclopent<1,3>oxazine

Base Information

Chemical Name:<4aR-(4aα,5β,6β,7β,7aα)>-2-<(2,3,4,6-Tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-7-(benzyloxy)-4,4a,5,6,7,7a-hexahydro-4a,5,6,7a-tetrahydroxycyclopent<1,3>oxazine
CAS No.:160344-07-0
Molecular Formula:C₄₈H₅₂N₂O₁₀
Molecular Weight:816.948
Hs Code.:

<4aR-(4aα,5β,6β,7β,7aα)>-2-<(2,3,4,6-Tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-7-(benzyloxy)-4,4a,5,6,7,7a-hexahydro-4a,5,6,7a-tetrahydroxycyclopent<d><1,3>oxazine

Synonyms:<4aR-(4aα,5β,6β,7β,7aα)>-2-<(2,3,4,6-Tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-7-(benzyloxy)-4,4a,5,6,7,7a-hexahydro-4a,5,6,7a-tetrahydroxycyclopent<1,3>oxazine

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Chemical Property of <4aR-(4aα,5β,6β,7β,7aα)>-2-<(2,3,4,6-Tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-7-(benzyloxy)-4,4a,5,6,7,7a-hexahydro-4a,5,6,7a-tetrahydroxycyclopent<1,3>oxazine

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Technology Process of <4aR-(4aα,5β,6β,7β,7aα)>-2-<(2,3,4,6-Tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-7-(benzyloxy)-4,4a,5,6,7,7a-hexahydro-4a,5,6,7a-tetrahydroxycyclopent<1,3>oxazine

There total 18 articles about <4aR-(4aα,5β,6β,7β,7aα)>-2-<(2,3,4,6-Tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-7-(benzyloxy)-4,4a,5,6,7,7a-hexahydro-4a,5,6,7a-tetrahydroxycyclopent<1,3>oxazine 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: 71.0%

: 160344-06-9
<1R-(1α,2β,3β,4β,5β)>-<4-(Benzyloxy)-1-(hydroxymethyl)-1,2,3-trihydroxycyclopent-5-yl>amino (2,3,4,6-O-tetrabenzyl-1-deoxy-α-D-glucopyranos-1-yl)amino thioketone

: 160344-07-0
<4aR-(4aα,5β,6β,7β,7aα)>-2-<(2,3,4,6-Tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-7-(benzyloxy)-4,4a,5,6,7,7a-hexahydro-4a,5,6,7a-tetrahydroxycyclopent<1,3>oxazine

Guidance literature:: With 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; In acetonitrile; at 0 - 5 ℃;
DOI:10.1016/S0040-4039(00)75990-9

Reference yield:

: 30725-00-9
2,3-O-isopropylidene-D-ribonic-γ-lactone

: 160344-07-0
<4aR-(4aα,5β,6β,7β,7aα)>-2-<(2,3,4,6-Tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-7-(benzyloxy)-4,4a,5,6,7,7a-hexahydro-4a,5,6,7a-tetrahydroxycyclopent<1,3>oxazine

Guidance literature:: Multi-step reaction with 14 steps

1: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 43 percent / DABCO / dimethylformamide / 1 h

4: 99 percent / CeCl₃*7H₂O, NaBH₄ / ethanol / 0.5 h / Ambient temperature

5: 84 percent / DMAP / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 30 min

6: 89 percent / 85percent m-chloroperoxybenzoic acid / CHCl₃ / 96 h / Ambient temperature

7: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.5 h / Ambient temperature

8: 92 percent / NaN₃, NH₄Cl / dimethylformamide / 16 h / 100 °C

9: 82 percent / p-TsOH*H₂O / dimethylformamide / 16 h / Ambient temperature

10: 100 percent / NaH / dimethylformamide; paraffin / 1 h / Ambient temperature

11: 1.) PPh₃, 2.) H₂O / 1.) THF, 7 d, 2.) r.t.

12: 2percent HCl / methanol / 4 h / 50 °C

13: Et₃N / tetrahydrofuran; H₂O / 2 h / Ambient temperature

14: 1.) 2-chloro-3-ethylbenzoxazolium tetrafluoroborate, 2.) Et₃N / 1.) MeCN, 0 deg C, 1 h, 2.) 0 deg C, 15 min

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; dmap; sodium tetrahydroborate; sodium azide; cerium(III) chloride; 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; water; hydrogen; sodium hydride; ammonium chloride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jo00095a021

Reference yield:

: 160343-80-6
<1S-(1α,4α,5α)>-1-<(Benzyloxycarbonyl)oxy>-3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,5-(isopropylidenedioxy)-2-cyclopentene

: 160344-07-0
<4aR-(4aα,5β,6β,7β,7aα)>-2-<(2,3,4,6-Tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-7-(benzyloxy)-4,4a,5,6,7,7a-hexahydro-4a,5,6,7a-tetrahydroxycyclopent<1,3>oxazine

Guidance literature:: Multi-step reaction with 9 steps

1: 89 percent / 85percent m-chloroperoxybenzoic acid / CHCl₃ / 96 h / Ambient temperature

2: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.5 h / Ambient temperature

3: 92 percent / NaN₃, NH₄Cl / dimethylformamide / 16 h / 100 °C

4: 82 percent / p-TsOH*H₂O / dimethylformamide / 16 h / Ambient temperature

5: 100 percent / NaH / dimethylformamide; paraffin / 1 h / Ambient temperature

6: 1.) PPh₃, 2.) H₂O / 1.) THF, 7 d, 2.) r.t.

7: 2percent HCl / methanol / 4 h / 50 °C

8: Et₃N / tetrahydrofuran; H₂O / 2 h / Ambient temperature

9: 1.) 2-chloro-3-ethylbenzoxazolium tetrafluoroborate, 2.) Et₃N / 1.) MeCN, 0 deg C, 1 h, 2.) 0 deg C, 15 min

With hydrogenchloride; sodium azide; 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; water; hydrogen; sodium hydride; ammonium chloride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jo00095a021