Reaction #696721

ord-e8797f5d9f0c431291b4abba57a54e69

Reaction equation

CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1ccc(=O)[nH]c1=O
Compound 1
CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1ccc(=O)[nH]c1=O
2'-O-methyluridine
CC[SiH](CC)CC
triethyl silane
FB(F)F
boron trifluoride
O=CC[C@H](O)[C@H](O)CO
2-deoxyribose
CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1ccc(=O)[nH]c1=O
compound 1
CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1ccc(=O)[nH]c1=O
2'-O-methyluridine
O=CC[C@H](O)[C@H](O)CO
2-deoxyribose
CC(=O)Cl
acetyl chloride
Cc1ccc(C(=O)Cl)cc1.c1ccncc1
p-toluoyl chloride pyridine
→
O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1
compound 2
O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1
uridine

Reactants

CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1ccc(=O)[nH]c1=O
Compound 1
CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1ccc(=O)[nH]c1=O
2'-O-methyluridine
CC[SiH](CC)CC
triethyl silane
FB(F)F
boron trifluoride
O=CC[C@H](O)[C@H](O)CO
2-deoxyribose
CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1ccc(=O)[nH]c1=O
compound 1
CO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1ccc(=O)[nH]c1=O
2'-O-methyluridine
O=CC[C@H](O)[C@H](O)CO
2-deoxyribose
CC(=O)Cl
acetyl chloride
Cc1ccc(C(=O)Cl)cc1.c1ccncc1
p-toluoyl chloride pyridine

Reagents

None

Solvents

CCO
ethanol
CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherto yield 1

Procedure

Referring to FIG. 17, commercially available 2-deoxyribose is converted to compound 1 in a two step process. In the first step, 2-deoxyribose is treated with a mixture of acetyl chloride and methanol. In the second step, the reaction mixture is treated with p-toluoyl chloride/pyridine mixture to yield 1. Compound 1 is incubated with a mixture of triethyl silane and boron trifluoride in ethanol to yield compound 2. Treatment of 4 with sodium methylate in methanol yield compound 3. Reacting 3 with t-butyl-diphenyl-silyl chloride in pyridine yields compound 4. The 3'-end of 4 is tritylated using 4,4'-dimethoxytrityl chloride in pyridine to yield compound 5. The 5'-protecting group in 5 can be removed using a mixture of triethylamine/hydrogen fluoride/DCM to yield 6.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05998203uspto-grants-1999_12