methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside

Base Information

• Chemical Name: methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside
• CAS No.: 3868-01-7
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.337
• Mol file: 3868-01-7.mol

Synonyms:methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside

Chemical Property of methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside

There total 16 articles about methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-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: 79.0%

methyl 2,6-dideoxy-3-O-benzyl-α-D-lyxo-hexopyranoside (107908-97-4) + methyl iodide (74-88-4) → methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside (3868-01-7)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

Reference yield:

(2R,3S,4R)-2,3-O-isopropylidene-6-hepten-2,3,4-triol (106062-13-9) → methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside (3868-01-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / NaH / tetrahydrofuran; dimethylformamide / 2 h / Heating

2: 98 percent / 4:1 HOAc-H₂O / 4 h / 100 °C

3: 1.) ozonolysis; 2.) acetyl chloride

4: 1.) KOH / 2.) 18-crown-6 / 1.) DMSO, 23 deg C, 1.5 h; 2.) 23 deg C, 4 h

With potassium hydroxide; water; sodium hydride; acetic acid; acetyl chloride; 18-crown-6 ether; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)84793-0

Reference yield:

(4S,5R)-4-((R)-1-Benzyloxy-but-3-enyl)-2,2,5-trimethyl-[1,3]dioxolane (106062-14-0) → methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside (3868-01-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / 4:1 HOAc-H₂O / 4 h / 100 °C

2: 1.) ozonolysis; 2.) acetyl chloride

3: 1.) KOH / 2.) 18-crown-6 / 1.) DMSO, 23 deg C, 1.5 h; 2.) 23 deg C, 4 h

With potassium hydroxide; water; acetic acid; acetyl chloride; 18-crown-6 ether;

DOI:10.1016/S0040-4039(00)84793-0

upstream raw materials:

methyl 2,6-dideoxy-3-O-benzyl-α-D-lyxo-hexopyranoside

methyl iodide

methyl 4-O-acetyl-3-O-benzyl-2,6-dideoxy-α-D-lyxo-hexopyranoside

methyl 2,6-dideoxy-α-D-lyxo-hexopyranoside

Downstream raw materials:

(2R,3S,4R)-4-Benzyloxy-3-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran

β-D-rubranitrose

α-D-rubranitrose

Acetic acid (2R,3S,4R,6S)-4-((2R,4R,5S,6R)-4-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester