(+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene ribonucleoside

Base Information

• Chemical Name: (+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene ribonucleoside
• CAS No.: 250699-09-3
• Molecular Formula: C₂₁H₂₆N₂O₆
• Molecular Weight: 402.447

Synonyms:(+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene ribonucleoside

Chemical Property of (+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene ribonucleoside

Chemical Property:

Purity/Quality:

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Technology Process of (+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene ribonucleoside

There total 4 articles about (+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene ribonucleoside 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: 46.2%

(+)-β-D-carbocyclic-1'-(1H-[N3-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl) ribonucleoside (250699-04-8) → (+)-β-D-carbocyclic-1'-(1H-[N3-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene ribonucleoside (250699-09-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 12h;

DOI:10.1080/07328319908044853

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (+)-β-D-carbocyclic-1'-(1H-[N3-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene ribonucleoside (250699-09-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide; dimethylsulfoxide / 5 h / 25 °C

1.2: 14.6 percent / dimethylformamide; dimethylsulfoxide / 25 °C

2.1: 85 percent / DEAD; Ph₃P / tetrahydrofuran / 13 h / -78 - 20 °C

3.1: 46.2 percent / TBAF / tetrahydrofuran / 12 h / 25 °C

With tetrabutyl ammonium fluoride; sodium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Substitution / 2.1: Mitsunobu coupling / 3.1: Desilylation;

DOI:10.1080/07328319908044853

Reference yield:

(1S,2S,3R,4S)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentanol (135486-55-4) → (+)-β-D-carbocyclic-1'-(1H-[N3-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene ribonucleoside (250699-09-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / DEAD; Ph₃P / tetrahydrofuran / 13 h / -78 - 20 °C

2: 46.2 percent / TBAF / tetrahydrofuran / 12 h / 25 °C

With tetrabutyl ammonium fluoride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1: Mitsunobu coupling / 2: Desilylation;

DOI:10.1080/07328319908044853

upstream raw materials:

(+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl) ribonucleoside

Benzyloxymethyl chloride

(1S,2S,3R,4S)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentanol

N³-benzyloxymethyluracil

Downstream raw materials:

(+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene-5'-O-(o-xylylenephosphate) ribonucleoside

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