<3aR-(3aα,4α,5β,6β,6aα)>-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-4,5,6-triol

Base Information

Chemical Name:<3aR-(3aα,4α,5β,6β,6aα)>-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-4,5,6-triol
CAS No.:160343-95-3
Molecular Formula:C₄₈H₅₂N₂O₁₀
Molecular Weight:816.948
Hs Code.:

<3aR-(3aα,4α,5β,6β,6aα)>-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-4,5,6-triol

Synonyms:<3aR-(3aα,4α,5β,6β,6aα)>-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-4,5,6-triol

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Chemical Property of <3aR-(3aα,4α,5β,6β,6aα)>-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-4,5,6-triol

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Technology Process of <3aR-(3aα,4α,5β,6β,6aα)>-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-4,5,6-triol

There total 17 articles about <3aR-(3aα,4α,5β,6β,6aα)>-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-4,5,6-triol 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:

: 5336-08-3
D-Ribono-1,4-lactone

: 160343-95-3
<3aR-(3aα,4α,5β,6β,6aα)>-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-4,5,6-triol

Guidance literature:: Multi-step reaction with 15 steps

1: 2.) 1 M aq. HCl / 1.) pyridinium p-toluenesulfonate / 1.) 50 deg C, 1 h, 2.) THF, 24 - 25 deg C, 1 h

2: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 43 percent / DABCO / dimethylformamide / 1 h

5: 99 percent / CeCl₃*7H₂O, NaBH₄ / ethanol / 0.5 h / Ambient temperature

6: 69 percent / NaH / dimethylformamide; paraffin / 3 h / Ambient temperature

7: 93 percent / n-Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

8: 100 percent / NaH / dimethylformamide; paraffin / 2 h / Ambient temperature

9: 55 percent / 85percent MCPBA / CHCl₃ / 24 h / Ambient temperature

10: 99 percent / DDQ, H₂O / CH₂Cl₂ / 3 h / 24 °C

11: 99 percent / NaN₃, NH₄Cl / dimethylformamide / 16 h / 100 °C

12: 1.) Ph₃P, 2.) H₂O / 1.) THF, r.t., 9 d, 2.) 16 h

13: 2percent HCl / methanol / 3 h / 50 °C

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

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

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; sodium tetrahydroborate; sodium azide; cerium(III) chloride; 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; tetrabutyl ammonium fluoride; water; sodium hydride; ammonium chloride; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jo00095a021

Reference yield:

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

: 160343-95-3
<3aR-(3aα,4α,5β,6β,6aα)>-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-4,5,6-triol

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: 69 percent / NaH / dimethylformamide; paraffin / 3 h / Ambient temperature

6: 93 percent / n-Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

7: 100 percent / NaH / dimethylformamide; paraffin / 2 h / Ambient temperature

8: 55 percent / 85percent MCPBA / CHCl₃ / 24 h / Ambient temperature

9: 99 percent / DDQ, H₂O / CH₂Cl₂ / 3 h / 24 °C

10: 99 percent / NaN₃, NH₄Cl / dimethylformamide / 16 h / 100 °C

11: 1.) Ph₃P, 2.) H₂O / 1.) THF, r.t., 9 d, 2.) 16 h

12: 2percent HCl / methanol / 3 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, 2 h, 2.) 0 deg C, 30 min

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; sodium tetrahydroborate; sodium azide; cerium(III) chloride; 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; tetrabutyl ammonium fluoride; water; sodium hydride; ammonium chloride; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jo00095a021

Reference yield:

: 93173-26-3
2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl isothiocyanate

: 160343-95-3
<3aR-(3aα,4α,5β,6β,6aα)>-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-4,5,6-triol

Guidance literature:: Multi-step reaction with 2 steps

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

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

With 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; triethylamine; In tetrahydrofuran; water;
DOI:10.1021/jo00095a021