(-)-(1R, 2S, 3R, 4R)-tert-butyl N-[2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentyl] carbamate

Base Information

• Chemical Name: (-)-(1R, 2S, 3R, 4R)-tert-butyl N-[2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentyl] carbamate
• CAS No.: 153064-90-5
• Molecular Formula: C₁₁H₂₁NO₅
• Molecular Weight: 247.291
• Mol file: 153064-90-5.mol

Synonyms:(-)-(1R, 2S, 3R, 4R)-tert-butyl N-[2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentyl] carbamate

Chemical Property of (-)-(1R, 2S, 3R, 4R)-tert-butyl N-[2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentyl] carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1R, 2S, 3R, 4R)-tert-butyl N-[2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentyl] carbamate

There total 1 articles about (-)-(1R, 2S, 3R, 4R)-tert-butyl N-[2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentyl] carbamate 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:

→ (1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxylmethyl)-1-aminocyclopentan hydrochloride (79200-57-0) + (-)-(1R, 2S, 3R, 4R)-tert-butyl N-[2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentyl] carbamate (153064-90-5)

Guidance literature:

Reference yield:

(-)-(1R, 2S, 3R, 4R)-tert-butyl N-[2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentyl] carbamate (153064-90-5) → {(1R,2S,3R,4R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-2-methoxymethoxy-cyclopentyl}-carbamic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 5.70 g / pyridine / 6 h / 20 °C

2: DIPEA / CH₂Cl₂ / 24 h / 20 °C

3: 0.444 g / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

4: pyridine / 0.17 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja050732x

Reference yield:

(-)-(1R, 2S, 3R, 4R)-tert-butyl N-[2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentyl] carbamate (153064-90-5) → N-1-{(1R,2S,3R,4R)-2-(methoxymethyloxy)-3-methoxy-4-(hydroxymethyl)cyclopentyl}-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine (859147-83-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 5.70 g / pyridine / 6 h / 20 °C

2.1: DIPEA / CH₂Cl₂ / 24 h / 20 °C

3.1: 0.444 g / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

4.1: pyridine / 0.17 h / 20 °C

5.1: NaH / tetrahydrofuran / 2 h / 0 °C

5.2: tetrahydrofuran / 1.33 h / 0 °C

6.1: 0.359 g / aq. AcOH / 1.17 h / 20 °C

7.1: 100 percent / water / 22 h / Heating

8.1: 78 percent / K₂CO₃ / methanol / 14 h / 20 °C

9.1: 95 percent / pyridine / 4 h / 20 °C

10.1: 100 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

11.1: 2,4,6-triisopropylbenzenesulfonyl chloride; pyridine / 1 h / 20 °C

11.2: 69 percent / pyridine / 1 h / 20 °C

12.1: 75 percent / aq. AcOH / 7 h / 20 °C

With pyridine; 2,4,6-triisopropylphenylsulfonyl chloride; tetrabutyl ammonium fluoride; water; sodium hydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja050732x

Downstream raw materials:

N-1-{(1R,2S,3R,4R)-2-(methoxymethyloxy)-3-methoxy-4-(hydroxymethyl)cyclopentyl}-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine

2-Benzoylamino-thiazole-5-carboxylic acid ((2R,3S,3aR,9aR)-5,5,7,7-tetraisopropyl-3-methoxy-hexahydro-4,6,8-trioxa-5,7-disila-cyclopentacycloocten-2-yl)-amide

2-Benzoylamino-thiazole-5-carboxylic acid {(1R,2S,3R,4R)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-2-methoxy-cyclopentyl}-amide

2-{[1-(2-Trimethylsilanyl-ethoxymethyl)-1H-pyrrole-2-carbonyl]-amino}-thiazole-5-carboxylic acid {(1R,2S,3R,4R)-4-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-2-methoxy-cyclopentyl}-amide

Refernces