<3aR-(3aα,4α,5β,6β,6aα)>-4-(Benzyloxy)-4-<(benzyloxy)methyl>-2-<(2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-5,6-diol

Base Information

Chemical Name:<3aR-(3aα,4α,5β,6β,6aα)>-4-(Benzyloxy)-4-<(benzyloxy)methyl>-2-<(2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-5,6-diol
CAS No.:160344-03-6
Molecular Formula:C₅₅H₅₈N₂O₁₀
Molecular Weight:907.073
Hs Code.:

<3aR-(3aα,4α,5β,6β,6aα)>-4-(Benzyloxy)-4-<(benzyloxy)methyl>-2-<(2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-5,6-diol

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Chemical Property of <3aR-(3aα,4α,5β,6β,6aα)>-4-(Benzyloxy)-4-<(benzyloxy)methyl>-2-<(2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-5,6-diol

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Technology Process of <3aR-(3aα,4α,5β,6β,6aα)>-4-(Benzyloxy)-4-<(benzyloxy)methyl>-2-<(2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-5,6-diol

There total 15 articles about <3aR-(3aα,4α,5β,6β,6aα)>-4-(Benzyloxy)-4-<(benzyloxy)methyl>-2-<(2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-5,6-diol 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:

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

: 160344-03-6
<3aR-(3aα,4α,5β,6β,6aα)>-4-(Benzyloxy)-4-<(benzyloxy)methyl>-2-<(2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-5,6-diol

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: 90 percent / NaH / dimethylformamide; tetrahydrofuran; paraffin / 16 h / Ambient temperature

11: 64 percent / 85percent aq. AcOH / 24 h / 40 - 45 °C

12: 89 percent / NaH / dimethylformamide; paraffin / 16 h / 10 °C

14: 1.) 2-chloro-3-ethylbenzoxazolium tetrafluoroborate, 2.) Et₃N / 1.) MeCN, 0 deg C, 1 h, 2.) 0 deg C, 15 min; r.t., 30 min

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

Reference yield:

: 160343-77-1
(Z)-5-O-(tert-Butyldimethylsilyl)-4,5-didehydro-2,3-O-isopropylidene-D-erythro-penturono-1,4-lactone

: 160344-03-6
<3aR-(3aα,4α,5β,6β,6aα)>-4-(Benzyloxy)-4-<(benzyloxy)methyl>-2-<(2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-5,6-diol

Guidance literature:: Multi-step reaction with 12 steps

2: 99 percent / CeCl₃*7H₂O, NaBH₄ / ethanol / 0.5 h / Ambient temperature

3: 84 percent / DMAP / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 30 min

4: 89 percent / 85percent m-chloroperoxybenzoic acid / CHCl₃ / 96 h / Ambient temperature

5: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.5 h / Ambient temperature

6: 92 percent / NaN₃, NH₄Cl / dimethylformamide / 16 h / 100 °C

7: 82 percent / p-TsOH*H₂O / dimethylformamide / 16 h / Ambient temperature

8: 90 percent / NaH / dimethylformamide; tetrahydrofuran; paraffin / 16 h / Ambient temperature

9: 64 percent / 85percent aq. AcOH / 24 h / 40 - 45 °C

10: 89 percent / NaH / dimethylformamide; paraffin / 16 h / 10 °C

12: 1.) 2-chloro-3-ethylbenzoxazolium tetrafluoroborate, 2.) Et₃N / 1.) MeCN, 0 deg C, 1 h, 2.) 0 deg C, 15 min; r.t., 30 min

With dmap; sodium tetrahydroborate; sodium azide; cerium(III) chloride; 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; hydrogen; sodium hydride; ammonium chloride; toluene-4-sulfonic acid; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jo00095a021

Reference yield:

: 160343-79-3
(3aS,4S,6aR)-6-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}-3a,6a-dihydro-2,2-dimethyl-4H-cyclopenta[d]-1,3-dioxol-4-ol

: 160344-03-6
<3aR-(3aα,4α,5β,6β,6aα)>-4-(Benzyloxy)-4-<(benzyloxy)methyl>-2-<(2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino>-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-5,6-diol

Guidance literature:: Multi-step reaction with 10 steps

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

2: 89 percent / 85percent m-chloroperoxybenzoic acid / CHCl₃ / 96 h / Ambient temperature

3: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.5 h / Ambient temperature

4: 92 percent / NaN₃, NH₄Cl / dimethylformamide / 16 h / 100 °C

5: 82 percent / p-TsOH*H₂O / dimethylformamide / 16 h / Ambient temperature

6: 90 percent / NaH / dimethylformamide; tetrahydrofuran; paraffin / 16 h / Ambient temperature

7: 64 percent / 85percent aq. AcOH / 24 h / 40 - 45 °C

8: 89 percent / NaH / dimethylformamide; paraffin / 16 h / 10 °C

10: 1.) 2-chloro-3-ethylbenzoxazolium tetrafluoroborate, 2.) Et₃N / 1.) MeCN, 0 deg C, 1 h, 2.) 0 deg C, 15 min; r.t., 30 min

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