Methyl 3,5-Di-O-benzyl-2-O-(trifluoromethanesulfonyl)-α-D-ribofuranoside

Base Information

• Chemical Name: Methyl 3,5-Di-O-benzyl-2-O-(trifluoromethanesulfonyl)-α-D-ribofuranoside
• CAS No.: 76832-95-6
• Molecular Formula: C₂₁H₂₃F₃O₇S
• Molecular Weight: 476.471

Synonyms:Methyl 3,5-Di-O-benzyl-2-O-(trifluoromethanesulfonyl)-α-D-ribofuranoside

Chemical Property of Methyl 3,5-Di-O-benzyl-2-O-(trifluoromethanesulfonyl)-α-D-ribofuranoside

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Technology Process of Methyl 3,5-Di-O-benzyl-2-O-(trifluoromethanesulfonyl)-α-D-ribofuranoside

There total 1 articles about Methyl 3,5-Di-O-benzyl-2-O-(trifluoromethanesulfonyl)-α-D-ribofuranoside 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: 20.0%

trifluoromethylsulfonic anhydride (358-23-6) + 1-O-methyl-3,5-di-O-benzyl-D-ribofuranoside (55775-39-8) → Methyl 3,5-Di-O-benzyl-2-O-(trifluoromethanesulfonyl)-β-D-ribofuranoside (76832-96-7) + Methyl 3,5-Di-O-benzyl-2-O-(trifluoromethanesulfonyl)-α-D-ribofuranoside (76832-95-6)

Guidance literature:

In pyridine; dichloromethane; at -15 ℃; for 2h;

DOI:10.1021/jo00322a007

Reference yield: 93.0%

Methyl 3,5-Di-O-benzyl-2-O-(trifluoromethanesulfonyl)-α-D-ribofuranoside (76832-95-6) → methyl 2-azido-3,5-di-O-benzyl-2-deoxy-α-D-arabinofuranoside (76833-00-6)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 2h;

DOI:10.1002/chem.201900651

Reference yield: 89.0%

Methyl 3,5-Di-O-benzyl-2-O-(trifluoromethanesulfonyl)-α-D-ribofuranoside (76832-95-6) → (2R,3R,4S,5S)-3-Benzyloxy-2-benzyloxymethyl-4-bromo-5-methoxy-tetrahydro-furan (76832-98-9)

Guidance literature:

With lithium bromide; In N,N,N,N,N,N-hexamethylphosphoric triamide; dimethyl sulfoxide; for 3h;

DOI:10.1021/jo00322a007

upstream raw materials:

trifluoromethylsulfonic anhydride

1-O-methyl-3,5-di-O-benzyl-D-ribofuranoside

Downstream raw materials:

Methyl 3,5-Di-O-benzyl-2-fluoro-2-deoxy-α-D-arabinofuranoside

(2R,3R,4S,5S)-3-Benzyloxy-2-benzyloxymethyl-4-chloro-5-methoxy-tetrahydro-furan

(2R,3R,4S,5S)-3-Benzyloxy-2-benzyloxymethyl-4-bromo-5-methoxy-tetrahydro-furan

(2R,3R,4S,5S)-3-Benzyloxy-2-benzyloxymethyl-4-iodo-5-methoxy-tetrahydro-furan

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