(3R/S)-(1S,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Base Information

• Chemical Name: (3R/S)-(1S,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
• CAS No.: 290348-24-2
• Molecular Formula: C₂₅H₂₆N₂O₆
• Molecular Weight: 450.491
• Mol file: 290348-24-2.mol

Synonyms:(3R/S)-(1S,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Chemical Property of (3R/S)-(1S,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3R/S)-(1S,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

There total 9 articles about (3R/S)-(1S,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 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: 57.0%

thymin (65-71-4,28806-14-6,691841-57-3) + methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside (219854-35-0) → (3R/S)-(1S,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (290348-24-2)

Guidance literature:

Multistep reaction.;

DOI:10.1002/1521-3765(20020201)8:3<712::AID-CHEM712>3.0.CO;2-0

Reference yield:

Methanesulfonic acid (2S,3S,4R)-3-benzyloxy-2-benzyloxymethyl-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester → (3R/S)-(1S,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (290348-24-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1039/b003104f

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → (3R/S)-(1S,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane (290348-24-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TMS-Cl; NO-bistrimethylsilylacetamide / acetonitrile

1.2: TMS-OTf / acetonitrile / 168 h / Heating

1.3: TBAF / tetrahydrofuran

2.1: NaH / dimethylformamide

With chloro-trimethyl-silane; sodium hydride; N,N-bis(trimethylsilyl)acetamide; In N,N-dimethyl-formamide; acetonitrile; 1.1: Silylation / 1.2: Coupling / 1.3: Deprotection / 2.1: Cyclization;

DOI:10.1039/b003104f

upstream raw materials:

thymin

(1S,3S,4R,7S)-7-Benzyloxy-1-benzyloxymethyl-3-phenylsulfanyl-2,5-dioxa-bicyclo[2.2.1]heptane

methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

Downstream raw materials:

(1R,3S,4R,7S)-3-(4-N-benzoyl-5-methylcytosin-1-yl)-1-(4,4'-dimethoxytrityl)oxymethyl-7-(O-2-cyanoethyl-N,N-diisopropylphosphityl)oxy-2,5-dioxabicyclo[2.2.1]heptane

(1R,3S,4R,7S)-3-(4-N-benzoyl-5-methylcytosin-1-yl)-7-(tert-butyldimethylsilyl)oxy-1-(4,4'-dimethoxytrityl)oxymethyl-2,5-dioxabicyclo[2.2.1]heptane

1-[1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-7-(tert-butyl-dimethyl-silanyloxy)-2,5-dioxa-bicyclo[2.2.1]hept-3-yl]-5-methyl-4-[1,2,4]triazol-1-yl-1H-pyrimidin-2-one

(1R,3S,4R,7S)-7-(tert-butyldimethylsilyloxy)-1-(4,4'-dimethoxytrityl)oxymethyl-3-(5-methylcytosin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane