6H-Furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one,2,3,3a,9a-tetrahydro-3-hydroxy-7-methyl-2-[(triphenylmethoxy)methyl]- (9CI)

Base Information

• Chemical Name: 6H-Furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one,2,3,3a,9a-tetrahydro-3-hydroxy-7-methyl-2-[(triphenylmethoxy)methyl]- (9CI)
• CAS No.: 22423-25-2
• Molecular Formula: C29H26 N2 O5
• Molecular Weight: 482.536

Synonyms:6H-Furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one,2,3,3a,9a-tetrahydro-3-hydroxy-7-methyl-2-[(trityloxy)methyl]- (7CI,8CI)

Chemical Property of 6H-Furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one,2,3,3a,9a-tetrahydro-3-hydroxy-7-methyl-2-[(triphenylmethoxy)methyl]- (9CI)

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6H-Furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one,2,3,3a,9a-tetrahydro-3-hydroxy-7-methyl-2-[(triphenylmethoxy)methyl]- (9CI)

There total 4 articles about 6H-Furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one,2,3,3a,9a-tetrahydro-3-hydroxy-7-methyl-2-[(triphenylmethoxy)methyl]- (9CI) 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: 93.0%

1-(5'-O-trityl-β-D-ribofuranosyl)thymine (101796-28-5) → 2,2'-anhydro-1-(5-O-trityl-β-D-arabinofuranosyl)thymine (22423-25-2)

Guidance literature:

With diethylamino-sulfur trifluoride; In 1,4-dioxane; at 20 ℃; for 0.666667h;

Reference yield: 73.0%

L-2,2'-anhydro-5-methyluridine (433733-92-7) + trityl chloride (76-83-5) → 2,2'-anhydro-1-(5-O-trityl-β-D-arabinofuranosyl)thymine (22423-25-2)

Guidance literature:

With pyridine; dmap; at 20 - 45 ℃; Product distribution / selectivity;

Reference yield: 12.0%

Benzoic acid (2R,3R,3aS,9aR)-7-methyl-6-oxo-2-trityloxymethyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3-yl ester → 2,2'-anhydro-1-(5-O-trityl-β-D-arabinofuranosyl)thymine (22423-25-2) + 1-(2-azido-2-deoxy-5-O-trityl-β-D-ribofuranosyl)thymine (151293-74-2) + 1-<2,3-N,O-carbonyl-2-deoxy-2-(phenylamino)-5-O-trityl-β-D-ribofuranosyl>thymine (151293-82-2) + 1-(2-azido-3-O-benzoyl-2-deoxy-5-O-trityl-β-D-ribofuranosyl)thymine (151293-73-1)

Guidance literature:

With lithium azide; In N,N-dimethyl-formamide; at 150 ℃; for 5h;

upstream raw materials:

1-(5'-O-trityl-β-D-ribofuranosyl)thymine

L-2,2'-anhydro-5-methyluridine

trityl chloride

Downstream raw materials:

Imidazole-1-carbothioic acid O-((2R,3R,3aS,9aR)-7-methyl-6-oxo-2-trityloxymethyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3-yl) ester

1-(2-azido-2-deoxy-3-O-mesyl-5-O-trityl-β-D-ribofuranosyl)thymine

5'-O-tritylthymidine

1-(3-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine

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