benzyl 5-O-(2,3-dideoxy-α-DL-threo-hex-2-enopyranosyl)-2,3-O-isopropylidene-β-D-ribofuranoside

Base Information

• Chemical Name: benzyl 5-O-(2,3-dideoxy-α-DL-threo-hex-2-enopyranosyl)-2,3-O-isopropylidene-β-D-ribofuranoside
• CAS No.: 64035-99-0
• Molecular Formula: C₂₁H₂₈O₈
• Molecular Weight: 408.449

Synonyms:benzyl 5-O-(2,3-dideoxy-α-DL-threo-hex-2-enopyranosyl)-2,3-O-isopropylidene-β-D-ribofuranoside

Chemical Property of benzyl 5-O-(2,3-dideoxy-α-DL-threo-hex-2-enopyranosyl)-2,3-O-isopropylidene-β-D-ribofuranoside

Chemical Property:

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Technology Process of benzyl 5-O-(2,3-dideoxy-α-DL-threo-hex-2-enopyranosyl)-2,3-O-isopropylidene-β-D-ribofuranoside

There total 3 articles about benzyl 5-O-(2,3-dideoxy-α-DL-threo-hex-2-enopyranosyl)-2,3-O-isopropylidene-β-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: 76.0%

3-Acetoxy-6-((3aR,4R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-3,6-dihydro-2H-pyran-2-carboxylic acid butyl ester (64035-93-4) → benzyl 5-O-(2,3-dideoxy-α-DL-threo-hex-2-enopyranosyl)-2,3-O-isopropylidene-β-D-ribofuranoside (64035-99-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 4h;

DOI:10.1016/S0008-6215(00)85244-1

Reference yield:

benzyl 2,3-O-isopropylidene-D-ribofuranoside (23276-32-6) → benzyl 5-O-(2,3-dideoxy-α-DL-threo-hex-2-enopyranosyl)-2,3-O-isopropylidene-β-D-ribofuranoside (64035-99-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / boron trifluoride etherate / acetonitrile / 3 h / 5 °C

2: 76 percent / LiAlH₄ / diethyl ether / 4 h

With lithium aluminium tetrahydride; boron trifluoride diethyl etherate; In diethyl ether; acetonitrile;

DOI:10.1016/S0008-6215(00)85244-1

Reference yield:

→ (2R,3R,6S)-6-((3aR,4R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol (64035-99-0)

Guidance literature:

entspr. α-Glykosid-uronsaeureester 3f, LiAlH4;

upstream raw materials:

3-Acetoxy-6-((3aR,4R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-3,6-dihydro-2H-pyran-2-carboxylic acid butyl ester

benzyl 2,3-O-isopropylidene-D-ribofuranoside

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