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

Base Information

• Chemical Name: (+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-thymin-1-yl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl) ribonucleoside
• CAS No.: 250699-03-7
• Molecular Formula: C₂₈H₄₂N₂O₆Si
• Molecular Weight: 530.737

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

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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (+)-β-D-carbocyclic-1'-(1H-[N³-benzyloxymethyl]-thymin-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: 96.2%

(1S,2S,3R,4S)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentanol (135486-55-4) + 3-((benzyloxy)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione (119451-90-0) → (+)-β-D-carbocyclic-1'-(1H-[N3-benzyloxymethyl]-thymin-1-yl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl) ribonucleoside (250699-03-7)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at -78 - 25 ℃; for 13h;

DOI:10.1080/07328319908044853

Reference yield: 42.5%

(+)-β-D-carbocyclic-1'-(1H-[N3-benzyloxymethyl]-thymin-1-yl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl) ribonucleoside (250699-03-7) → (+)-β-D-carbocyclic-1'-(1H-[N3-benzyloxymethyl]-thymin-1-yl)-2',3'-O-isopropylidene ribonucleoside (250699-08-2)

Guidance literature:

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

DOI:10.1080/07328319908044853

Reference yield:

(+)-β-D-carbocyclic-1'-(1H-[N3-benzyloxymethyl]-thymin-1-yl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl) ribonucleoside (250699-03-7) → (+)-β-D-carbocyclic-1'-(1H-[N3-benzyloxymethyl]-thymin-1-yl)-2',3'-O-isopropylidene-5'-O-(o-xylylenephosphite) ribonucleoside

Guidance literature:

Multi-step reaction with 2 steps

1: 42.5 percent / TBAF / tetrahydrofuran / 12 h / 25 °C

2: 1H-tetrazole / tetrahydrofuran / 14 h

With 1H-tetrazole; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1: Desilylation / 2: Phosphitylation;

DOI:10.1080/07328319908044853

upstream raw materials:

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

3-((benzyloxy)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Downstream raw materials:

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

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

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