<1R-(1α,2β,3β,4β,5β)>-<1-(Benzyloxy)-1-<(benzyloxy)methyl>-2,3,4-trihydroxycyclopent-5-yl>amino (2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino thioketone

Base Information

Chemical Name:<1R-(1α,2β,3β,4β,5β)>-<1-(Benzyloxy)-1-<(benzyloxy)methyl>-2,3,4-trihydroxycyclopent-5-yl>amino (2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino thioketone
CAS No.:160344-02-5
Molecular Formula:C₅₅H₆₀N₂O₁₀S
Molecular Weight:941.155
Hs Code.:

<1R-(1α,2β,3β,4β,5β)>-<1-(Benzyloxy)-1-<(benzyloxy)methyl>-2,3,4-trihydroxycyclopent-5-yl>amino (2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino thioketone

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Chemical Property of <1R-(1α,2β,3β,4β,5β)>-<1-(Benzyloxy)-1-<(benzyloxy)methyl>-2,3,4-trihydroxycyclopent-5-yl>amino (2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino thioketone

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Technology Process of <1R-(1α,2β,3β,4β,5β)>-<1-(Benzyloxy)-1-<(benzyloxy)methyl>-2,3,4-trihydroxycyclopent-5-yl>amino (2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino thioketone

There total 14 articles about <1R-(1α,2β,3β,4β,5β)>-<1-(Benzyloxy)-1-<(benzyloxy)methyl>-2,3,4-trihydroxycyclopent-5-yl>amino (2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino thioketone 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

: 160344-02-5
<1R-(1α,2β,3β,4β,5β)>-<1-(Benzyloxy)-1-<(benzyloxy)methyl>-2,3,4-trihydroxycyclopent-5-yl>amino (2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino thioketone

Guidance literature:: Multi-step reaction with 13 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

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; sodium tetrahydroborate; sodium azide; cerium(III) chloride; hydrogen; sodium hydride; ammonium chloride; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; 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

: 160344-02-5
<1R-(1α,2β,3β,4β,5β)>-<1-(Benzyloxy)-1-<(benzyloxy)methyl>-2,3,4-trihydroxycyclopent-5-yl>amino (2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino thioketone

Guidance literature:: Multi-step reaction with 9 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

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

Reference yield:

: 160343-78-2
(3aR,6aR)-6-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}-3a,6a-dihydro-2,2-dimethyl-4H-cyclopenta[d]-1,3-dioxol-4-one

: 160344-02-5
<1R-(1α,2β,3β,4β,5β)>-<1-(Benzyloxy)-1-<(benzyloxy)methyl>-2,3,4-trihydroxycyclopent-5-yl>amino (2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranos-1-yl)amino thioketone

Guidance literature:: Multi-step reaction with 10 steps

1: 99 percent / CeCl₃*7H₂O, NaBH₄ / ethanol / 0.5 h / Ambient temperature

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

3: 89 percent / 85percent m-chloroperoxybenzoic acid / CHCl₃ / 96 h / Ambient temperature

4: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.5 h / Ambient temperature

5: 92 percent / NaN₃, NH₄Cl / dimethylformamide / 16 h / 100 °C

6: 82 percent / p-TsOH*H₂O / dimethylformamide / 16 h / Ambient temperature

7: 90 percent / NaH / dimethylformamide; tetrahydrofuran; paraffin / 16 h / Ambient temperature

8: 64 percent / 85percent aq. AcOH / 24 h / 40 - 45 °C

9: 89 percent / NaH / dimethylformamide; paraffin / 16 h / 10 °C

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