2,3,4-trideoxy-2',3',4',5'-tetrahydro-4'-oxo-6-O-trityl-(tert-butyl α-D-ribo-hexopyranosido)<2,3-b>furan

Base Information

• Chemical Name: 2,3,4-trideoxy-2',3',4',5'-tetrahydro-4'-oxo-6-O-trityl-(tert-butyl α-D-ribo-hexopyranosido)<2,3-b>furan
• CAS No.: 135195-32-3
• Molecular Formula: C₃₁H₃₄O₅
• Molecular Weight: 486.608
• Mol file: 135195-32-3.mol

Synonyms:2,3,4-trideoxy-2',3',4',5'-tetrahydro-4'-oxo-6-O-trityl-(tert-butyl α-D-ribo-hexopyranosido)<2,3-b>furan

Chemical Property of 2,3,4-trideoxy-2',3',4',5'-tetrahydro-4'-oxo-6-O-trityl-(tert-butyl α-D-ribo-hexopyranosido)<2,3-b>furan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4-trideoxy-2',3',4',5'-tetrahydro-4'-oxo-6-O-trityl-(tert-butyl α-D-ribo-hexopyranosido)<2,3-b>furan

There total 3 articles about 2,3,4-trideoxy-2',3',4',5'-tetrahydro-4'-oxo-6-O-trityl-(tert-butyl α-D-ribo-hexopyranosido)<2,3-b>furan 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: 90.0%

[(3aS,5S,7R,7aR)-7-tert-Butoxy-5-trityloxymethyl-tetrahydro-furo[2,3-c]pyran-(3Z)-ylidenemethyl]-tributyl-stannane (135195-31-2,135269-47-5) → 2,3,4-trideoxy-2',3',4',5'-tetrahydro-4'-oxo-6-O-trityl-(tert-butyl α-D-ribo-hexopyranosido)<2,3-b>furan (135195-32-3)

Guidance literature:

With sodium periodate; osmium(VIII) oxide; In diethyl ether; water;

DOI:10.1016/S0040-4039(00)74333-4

Reference yield:

tert-butyl 3,4-dideoxy-2-O-(prop-2'-ynyl)-6-O-trityl-α-D-erythro-hex-3-enopyranoside (135195-24-3) → 2,3,4-trideoxy-2',3',4',5'-tetrahydro-4'-oxo-6-O-trityl-(tert-butyl α-D-ribo-hexopyranosido)<2,3-b>furan (135195-32-3)

Guidance literature:

With sodium periodate; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; Yield given. Multistep reaction; 1) benzene, reflux, 2) t-BuOH, Et₂O, H₂O, 2h;

Reference yield:

tert-butyl 3,4-dideoxy-6-O-trityl-α-D-erythro-hex-3-enopyranoside (142344-15-8) → 2,3,4-trideoxy-2',3',4',5'-tetrahydro-4'-oxo-6-O-trityl-(tert-butyl α-D-ribo-hexopyranosido)<2,3-b>furan (135195-32-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) NaH / 1) THF, 30 min, 2a) 0 deg C, 30 min, 2b) RT

2: 1) Bu₃SnH, AIBN, 2) OsO₄, NaIO₄ / 1) benzene, reflux, 2) t-BuOH, Et₂O, H₂O, 2h

With sodium periodate; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride;

upstream raw materials:

[(3aS,5S,7R,7aR)-7-tert-Butoxy-5-trityloxymethyl-tetrahydro-furo[2,3-c]pyran-(3Z)-ylidenemethyl]-tributyl-stannane

tert-butyl 3,4-dideoxy-2-O-(prop-2'-ynyl)-6-O-trityl-α-D-erythro-hex-3-enopyranoside

tert-butyl 3,4-dideoxy-6-O-trityl-α-D-erythro-hex-3-enopyranoside