methyl 2,3,4-trideoxy-2,4-di-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside

Base Information

• Chemical Name: methyl 2,3,4-trideoxy-2,4-di-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside
• CAS No.: 73679-58-0
• Molecular Formula: C₂₈H₃₂O₃
• Molecular Weight: 416.56
• Mol file: 73679-58-0.mol

Synonyms:methyl 2,3,4-trideoxy-2,4-di-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside

Chemical Property of methyl 2,3,4-trideoxy-2,4-di-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4-trideoxy-2,4-di-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside

There total 20 articles about methyl 2,3,4-trideoxy-2,4-di-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside 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:

methyl 2,3,4-trideoxy-4-C-methyl-2-C-methylene-6-O-(triphenylmethyl)-α-D-threo-hexopyranoside (73656-98-1) → methyl 2,3,4-trideoxy-2,4-di-C-methyl-6-O-(triphenylmethyl)-α-D-lyxo-hexopyranoside (68880-95-5) + methyl 2,3,4-trideoxy-2,4-di-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside (73679-58-0)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethyl acetate; Yield given; Ambient temperature; other catalysts;

DOI:10.1021/jo00345a008

Reference yield:

(2S,6S)-2-Methoxy-6-trityloxymethyl-6H-pyran-3-one (35303-94-7) → methyl 2,3,4-trideoxy-2,4-di-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside (73679-58-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / dimethyl sulfide-copper bromide / diethyl ether / 1.) -78 deg C, 0.5 h, 2.) -40 deg C, 0.5 h

2: n-butyllithium / 1.) diethyl ether, room temp., 1 h, 2.) 6 h

3: H₂ / W-8 Raney nickel / ethyl acetate / Ambient temperature; other catalyst

With n-butyllithium; copper(I) bromide dimethylsulfide complex; hydrogen; W-8 Raney nickel; In diethyl ether; ethyl acetate;

DOI:10.1021/jo00345a008

Reference yield:

methyl 3,4-dideoxy-4-C-methyl-6-O-(triphenylmethyl)-α-D-threo-hexopyranosid-2-ulose (66149-56-2) → methyl 2,3,4-trideoxy-2,4-di-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside (73679-58-0)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium / 1.) diethyl ether, room temp., 1 h, 2.) 6 h

2: H₂ / W-8 Raney nickel / ethyl acetate / Ambient temperature; other catalyst

With n-butyllithium; hydrogen; W-8 Raney nickel; In ethyl acetate;

DOI:10.1021/jo00345a008

upstream raw materials:

(2S,3R,6S)-2-Methoxy-3-methyl-5-methylene-6-trityloxymethyl-tetrahydro-pyran

methyl 2,3,4-trideoxy-4-C-methyl-2-C-methylene-6-O-(triphenylmethyl)-α-D-threo-hexopyranoside

(2S,3R,5S,6S)-2-Methoxy-3,5-dimethyl-6-trityloxymethyl-tetrahydro-pyran-4-ol

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altropyranoside

Downstream raw materials:

Toluene-4-sulfonic acid (1S,2R,4R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-[1,3]dithian-2-yl-2-methyl-pentyl ester