(1R,2R,4R)-1-tert-butoxycarbonylamino-2-hydroxy-4-[(6-dimethoxytrityl)oxymethyl]cyclopentane

Base Information

• Chemical Name: (1R,2R,4R)-1-tert-butoxycarbonylamino-2-hydroxy-4-[(6-dimethoxytrityl)oxymethyl]cyclopentane
• CAS No.: 859147-43-6
• Molecular Formula: C₃₂H₃₉NO₆
• Molecular Weight: 533.665

Synonyms:(1R,2R,4R)-1-tert-butoxycarbonylamino-2-hydroxy-4-[(6-dimethoxytrityl)oxymethyl]cyclopentane

Chemical Property of (1R,2R,4R)-1-tert-butoxycarbonylamino-2-hydroxy-4-[(6-dimethoxytrityl)oxymethyl]cyclopentane

Chemical Property:

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Technology Process of (1R,2R,4R)-1-tert-butoxycarbonylamino-2-hydroxy-4-[(6-dimethoxytrityl)oxymethyl]cyclopentane

There total 2 articles about (1R,2R,4R)-1-tert-butoxycarbonylamino-2-hydroxy-4-[(6-dimethoxytrityl)oxymethyl]cyclopentane 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: 87.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + (1R,2R,4S)-1-tert-butoxycarbonylamino-2-hydroxy-4-hydroxymethylcyclopentane (859147-41-4) → (1R,2R,4R)-1-tert-butoxycarbonylamino-2-hydroxy-4-[(6-dimethoxytrityl)oxymethyl]cyclopentane (859147-43-6)

Guidance literature:

With pyridine; at 20 ℃; for 0.0833333h;

DOI:10.1021/ja050732x

Reference yield:

tert-butyl N-[(1S,2R,4R,5R)-4-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-yl]carbamate (244057-71-4) → (1R,2R,4R)-1-tert-butoxycarbonylamino-2-hydroxy-4-[(6-dimethoxytrityl)oxymethyl]cyclopentane (859147-43-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / Red-Al / CH₂Cl₂; toluene / 23 h / 0 °C

2: 87 percent / pyridine / 0.08 h / 20 °C

With pyridine; sodium bis(2-methoxyethoxy)aluminium dihydride; In dichloromethane; toluene;

DOI:10.1021/ja050732x

Reference yield: 96.0%

(1R,2R,4R)-1-tert-butoxycarbonylamino-2-hydroxy-4-[(6-dimethoxytrityl)oxymethyl]cyclopentane (859147-43-6) + chloromethyl methyl ether (107-30-2) → (1R,2R,4R)-1-t-butoxycarbonylamino-2-(methoxymethyloxy)-4-[(6-dimethoxytrityl)oxymethyl]cyclopentane (859147-44-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 23h;

DOI:10.1021/ja050732x

upstream raw materials:

4,4'-dimethoxytrityl chloride

(1R,2R,4S)-1-tert-butoxycarbonylamino-2-hydroxy-4-hydroxymethylcyclopentane

tert-butyl N-[(1S,2R,4R,5R)-4-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-yl]carbamate

Downstream raw materials:

(1R,2R,4R)-1-t-butoxycarbonylamino-2-(methoxymethyloxy)-4-[(6-dimethoxytrityl)oxymethyl]cyclopentane

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

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