<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

Base Information

Chemical Name:<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
CAS No.:160344-06-9
Molecular Formula:C₄₈H₅₄N₂O₁₀S
Molecular Weight:851.03
Hs Code.:

<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

Synonyms:<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

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Chemical Property of <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

Chemical Property:

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Technology Process of <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

There total 16 articles about <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 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

: 160344-06-9
<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

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: 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

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; dmap; sodium tetrahydroborate; sodium azide; cerium(III) chloride; 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

: 160344-06-9
<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

Guidance literature:: Multi-step reaction with 8 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

With hydrogenchloride; sodium azide; 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

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

: 160344-06-9
<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

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

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

9: 2percent HCl / methanol / 4 h / 50 °C

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

With hydrogenchloride; dmap; sodium tetrahydroborate; sodium azide; cerium(III) chloride; water; hydrogen; sodium hydride; ammonium chloride; 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