methyl 2,4-dideoxy-2-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside

Base Information

• Chemical Name: methyl 2,4-dideoxy-2-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside
• CAS No.: 145798-80-7
• Molecular Formula: C₂₇H₃₀O₄
• Molecular Weight: 418.533
• Mol file: 145798-80-7.mol

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

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

There total 9 articles about methyl 2,4-dideoxy-2-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: 83.0%

methyl 3,4-anhydro-2-deoxy-2-C-methyl-6-O-trityl-α-D-altropyranoside (118360-84-2) → methyl 2,3-dideoxy-2-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside (68880-92-2) + methyl 2,4-dideoxy-2-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside (145798-80-7)

Guidance literature:

With sodium tetrahydroborate; bis-(1,2-dimethylpropyl)borane; In tetrahydrofuran; at 25 ℃; for 24h; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)79452-4

Reference yield:

trityl chloride (76-83-5) → methyl 2,4-dideoxy-2-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside (145798-80-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 4-dimethylaminopyridine, pyridine / 24 h / 25 °C

2: 8 h / 25 °C

3: NaOMe / methanol; dioxane / 14 h / 25 °C

4: 80 percent / LiBr / dioxane / 72 h / 110 °C

5: 86 percent / CH₂Cl₂; diethyl ether / 0.75 h / Ambient temperature

6: 89 percent / NaH / dimethylformamide / 1 h / 0 °C

7: LiBH₄ / tetrahydrofuran / 21 h / 25 °C

With pyridine; dmap; lithium borohydride; sodium methylate; sodium hydride; lithium bromide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.65.2974

Reference yield:

methyl 4-bromo-2,4-dideoxy-2-C-methyl-6-O-triphenylmethyl-α-D-idopyranoside (118360-81-9) → methyl 2,4-dideoxy-2-C-methyl-6-O-(triphenylmethyl)-α-D-arabino-hexopyranoside (145798-80-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / NaH / dimethylformamide / 1 h / 0 °C

2: LiBH₄ / tetrahydrofuran / 21 h / 25 °C

With lithium borohydride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.65.2974

upstream raw materials:

methyl 3,4-anhydro-2-deoxy-2-C-methyl-6-O-trityl-α-D-altropyranoside

trityl chloride

methyl 4-bromo-2,4-dideoxy-2-C-methyl-6-O-triphenylmethyl-α-D-idopyranoside

methyl 2,3-anhydro-4-bromo-4-deoxy-6-O-trityl-α-D-gulopyranoside