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

Base Information

• Chemical Name: (+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl) ribonucleoside
• CAS No.: 250699-04-8
• Molecular Formula: C₂₇H₄₀N₂O₆Si
• Molecular Weight: 516.71

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

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

Chemical Property:

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

There total 2 articles about (+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl) 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: 85.0%

(1S,2S,3R,4S)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentanol (135486-55-4) + N3-benzyloxymethyluracil (250699-19-5) → (+)-β-D-carbocyclic-1'-(1H-[N3-benzyloxymethyl]-uracil-1-yl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl) ribonucleoside (250699-04-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at -78 - 20 ℃; for 13h;

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-5'-O-(tert-butyldimethylsilyl) ribonucleoside (250699-04-8)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1080/07328319908044853

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

upstream raw materials:

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

N³-benzyloxymethyluracil

Benzyloxymethyl chloride

Downstream raw materials:

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

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

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