(1R,2R,3S,4S)-1-bromo-2-O-(N-benzylcarbamoyl)-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

Base Information

Chemical Name:(1R,2R,3S,4S)-1-bromo-2-O-(N-benzylcarbamoyl)-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol
CAS No.:732308-54-2
Molecular Formula:C₁₇H₂₀BrNO₄
Molecular Weight:382.254
Hs Code.:

Synonyms:(1R,2R,3S,4S)-1-bromo-2-O-(N-benzylcarbamoyl)-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

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Chemical Property of (1R,2R,3S,4S)-1-bromo-2-O-(N-benzylcarbamoyl)-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

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Technology Process of (1R,2R,3S,4S)-1-bromo-2-O-(N-benzylcarbamoyl)-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

There total 7 articles about (1R,2R,3S,4S)-1-bromo-2-O-(N-benzylcarbamoyl)-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: 69.0%

: 3173-56-6
benzyl isothiocyanate

: 732308-53-1
(1R,2R,3R,4S)-1-bromo-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

: 732308-54-2
(1R,2R,3S,4S)-1-bromo-2-O-(N-benzylcarbamoyl)-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

Guidance literature:: With triethylamine; In dichloromethane; at 25 ℃;
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

: 732308-54-2
(1R,2R,3S,4S)-1-bromo-2-O-(N-benzylcarbamoyl)-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

Guidance literature:: Multi-step reaction with 7 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: 53 percent / LiBr / acetic acid / 2 h / 20 °C

7.1: 69 percent / Et₃N / CH₂Cl₂ / 25 °C

With sodium hydroxide; n-butyllithium; dihydrogen peroxide; sodium amide; triethylamine; pyridinium chlorochromate; lithium bromide; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid; acetone; benzene;
DOI:10.1039/b315704k

Reference yield:

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

: 732308-54-2
(1R,2R,3S,4S)-1-bromo-2-O-(N-benzylcarbamoyl)-3,4-O-isopropylidene-5-methylenecyclopentane-2,3,4-triol

Guidance literature:: Multi-step reaction with 6 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: 53 percent / LiBr / acetic acid / 2 h / 20 °C

6.1: 69 percent / Et₃N / CH₂Cl₂ / 25 °C

With sodium hydroxide; n-butyllithium; dihydrogen peroxide; sodium amide; triethylamine; pyridinium chlorochromate; lithium bromide; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid; benzene;
DOI:10.1039/b315704k