(1R,2S,3R,4S)-1-(N-benzyl)-(N-tert-butoxycarbonyl)amino-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

Base Information

Chemical Name:(1R,2S,3R,4S)-1-(N-benzyl)-(N-tert-butoxycarbonyl)amino-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol
CAS No.:732308-51-9
Molecular Formula:C₂₁H₂₉NO₅
Molecular Weight:375.465
Hs Code.:

Synonyms:(1R,2S,3R,4S)-1-(N-benzyl)-(N-tert-butoxycarbonyl)amino-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

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Chemical Property of (1R,2S,3R,4S)-1-(N-benzyl)-(N-tert-butoxycarbonyl)amino-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

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Technology Process of (1R,2S,3R,4S)-1-(N-benzyl)-(N-tert-butoxycarbonyl)amino-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

There total 6 articles about (1R,2S,3R,4S)-1-(N-benzyl)-(N-tert-butoxycarbonyl)amino-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-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:

: 24424-99-5
di-tert-butyl dicarbonate

: 100-46-9
benzylamine

: 247191-05-5
(2S,3S,4S,5R)-1-methylene-2,3-O-isopropylidene-2,3-dihydroxy-4,5-epoxycyclopentane

: 732308-51-9
(1R,2S,3R,4S)-1-(N-benzyl)-(N-tert-butoxycarbonyl)amino-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

Guidance literature:: benzylamine; (2S,3S,4S,5R)-1-methylene-2,3-O-isopropylidene-2,3-dihydroxy-4,5-epoxycyclopentane; at 25 ℃; for 1.5h;

di-tert-butyl dicarbonate; With sodium hydrogencarbonate; In ethyl acetate; Further stages.;
DOI:10.1039/b315704k

Reference yield:

: 4099-88-1,67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1
(3aS,6R,6aS)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol

: 732308-51-9
(1R,2S,3R,4S)-1-(N-benzyl)-(N-tert-butoxycarbonyl)amino-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

Guidance literature:: Multi-step reaction with 6 steps

1.1: acetone / 3 h / 25 °C

2.1: 39 percent / pyridinium chlorochromate / benzene / Heating

3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C

3.2: 39 percent / tetrahydrofuran; hexane / 2.83 h / -78 - -20 °C

4.1: 79 percent / aq. H₂O₂; NaOH / methanol / 1 h / -50 °C

5.1: 100 percent / NaNH₂ / tetrahydrofuran / 1 h / 25 °C

6.1: 1.5 h / 25 °C

6.2: 36 mg / aq. NaHCO₃ / ethyl acetate

With sodium hydroxide; n-butyllithium; dihydrogen peroxide; sodium amide; pyridinium chlorochromate; In tetrahydrofuran; methanol; hexane; acetone; benzene;
DOI:10.1039/b315704k

Reference yield:

: 63029-07-2,828937-29-7
methyl 2,3-O-isopropylidene-α-D-lyxofuranoside

: 732308-51-9
(1R,2S,3R,4S)-1-(N-benzyl)-(N-tert-butoxycarbonyl)amino-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 39 percent / pyridinium chlorochromate / benzene / Heating

2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C

2.2: 39 percent / tetrahydrofuran; hexane / 2.83 h / -78 - -20 °C

3.1: 79 percent / aq. H₂O₂; NaOH / methanol / 1 h / -50 °C

4.1: 100 percent / NaNH₂ / tetrahydrofuran / 1 h / 25 °C

5.1: 1.5 h / 25 °C

5.2: 36 mg / aq. NaHCO₃ / ethyl acetate

With sodium hydroxide; n-butyllithium; dihydrogen peroxide; sodium amide; pyridinium chlorochromate; In tetrahydrofuran; methanol; hexane; benzene;
DOI:10.1039/b315704k