(2S,3S,4R,5R)-1-benzyloxycarbonyl-2-hydroxymethyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

Base Information

Chemical Name:(2S,3S,4R,5R)-1-benzyloxycarbonyl-2-hydroxymethyl-3,4-isopropylidenedioxy-5-methylpyrrolidine
CAS No.:264234-50-6
Molecular Formula:C₁₇H₂₃NO₅
Molecular Weight:321.373
Hs Code.:

Synonyms:(2S,3S,4R,5R)-1-benzyloxycarbonyl-2-hydroxymethyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

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Chemical Property of (2S,3S,4R,5R)-1-benzyloxycarbonyl-2-hydroxymethyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

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Technology Process of (2S,3S,4R,5R)-1-benzyloxycarbonyl-2-hydroxymethyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

There total 14 articles about (2S,3S,4R,5R)-1-benzyloxycarbonyl-2-hydroxymethyl-3,4-isopropylidenedioxy-5-methylpyrrolidine 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:

: 188242-67-3
2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-allose

: 264234-50-6
(2S,3S,4R,5R)-1-benzyloxycarbonyl-2-hydroxymethyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

Guidance literature:: With sodium tetrahydroborate; In ethanol;
DOI:10.1016/S0957-4166(97)00008-6

Reference yield:

: 173829-12-4
(3R,4R,5R,6R)-6-Dimethoxymethyl-4,5-dihydroxy-3-methyl-[1,2]oxazinane-2-carboxylic acid benzyl ester

: 264234-50-6
(2S,3S,4R,5R)-1-benzyloxycarbonyl-2-hydroxymethyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / Amberlyst-15 (H⁺) / 2 h / 40 °C

2: H₂ / Pd/C / ethanol / 24 h / 50 °C

3: 1.55 g / NaOH / H₂O / 3 h / 20 °C

4: 100 percent / Et₃N / CH₂Cl₂ / 1 h / -10 °C

5: 1.03 g / NaOH / ethanol; H₂O / 36 h / 80 °C

6: Amberlyst-15 (H⁺) / acetone / 1 h / 40 °C

7: Na₂CO₃ / methanol / 1 h / 20 °C

8: 0.49 g / NaBH₄ / methanol / 0.25 h

With sodium hydroxide; sodium tetrahydroborate; Amberlyst-15 (H⁺); hydrogen; sodium carbonate; triethylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; acetone; 1: Substitution / 2: Catalytic hydrogenation / 3: Substitution / 4: Substitution / 5: Cyclization / 6: Acetal removing / 7: Isomerization / 8: Reduction;
DOI:10.1016/S0040-4020(99)01078-9

Reference yield:

: 188242-60-6
benzyl (3R)-t-4,t-5-isopropylidenedioxy-c-6-dimethoxymethyl-r-3-methyl-1,2-oxazane-2-carboxylate

: 264234-50-6
(2S,3S,4R,5R)-1-benzyloxycarbonyl-2-hydroxymethyl-3,4-isopropylidenedioxy-5-methylpyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: H₂ / Pd/C / ethanol / 24 h / 50 °C

2: 1.55 g / NaOH / H₂O / 3 h / 20 °C

3: 100 percent / Et₃N / CH₂Cl₂ / 1 h / -10 °C

4: 1.03 g / NaOH / ethanol; H₂O / 36 h / 80 °C

5: Amberlyst-15 (H⁺) / acetone / 1 h / 40 °C

6: Na₂CO₃ / methanol / 1 h / 20 °C

7: 0.49 g / NaBH₄ / methanol / 0.25 h

With sodium hydroxide; sodium tetrahydroborate; Amberlyst-15 (H⁺); hydrogen; sodium carbonate; triethylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; acetone; 1: Catalytic hydrogenation / 2: Substitution / 3: Substitution / 4: Cyclization / 5: Acetal removing / 6: Isomerization / 7: Reduction;
DOI:10.1016/S0040-4020(99)01078-9