methyl 2,4-di-O-benzyl-α-D-tyvelopyranoside

Base Information

• Chemical Name: methyl 2,4-di-O-benzyl-α-D-tyvelopyranoside
• CAS No.: 187746-19-6
• Molecular Formula: C₂₁H₂₆O₄
• Molecular Weight: 342.435
• Mol file: 187746-19-6.mol

Synonyms:

Chemical Property of methyl 2,4-di-O-benzyl-α-D-tyvelopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,4-di-O-benzyl-α-D-tyvelopyranoside

There total 7 articles about methyl 2,4-di-O-benzyl-α-D-tyvelopyranoside 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 2,4-di-O-benzyl-3-O-(methylthio)thiocarbonyl-α-D-rhamnopyranoside (603962-17-0) → methyl 2,4-di-O-benzyl-α-D-tyvelopyranoside (187746-19-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 115 ℃; for 3h;

DOI:10.1246/bcsj.76.1409

Reference yield:

methyl 2,4-di-O-benzyl-α-D-mannopyranoside (58341-67-6,67381-34-4,86172-91-0,86342-19-0,67381-29-7) → methyl 2,4-di-O-benzyl-α-D-tyvelopyranoside (187746-19-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 378 mg / pyridine / -15 - 25 °C

2: 129.7 mg / LiAlH₄ / diethyl ether / 0.5 h / Heating

3: imidazol; NaH / tetrahydrofuran / 3.5 h / 20 °C

4: 45.4 mg / tetrahydrofuran / 20 °C

5: 9.0 mg / n-Bu₃SnH; AIBN / toluene / 3 h / 115 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1246/bcsj.76.1409

Reference yield:

methyl 2,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside (112612-46-1) → methyl 2,4-di-O-benzyl-α-D-tyvelopyranoside (187746-19-6)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazol; NaH / tetrahydrofuran / 3.5 h / 20 °C

2: 45.4 mg / tetrahydrofuran / 20 °C

3: 9.0 mg / n-Bu₃SnH; AIBN / toluene / 3 h / 115 °C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; toluene;

DOI:10.1246/bcsj.76.1409

upstream raw materials:

methyl 3,6-dideoxy-α-D-arabino-hexopyranoside

benzyl bromide

methyl 2,4-di-O-benzyl-3-O-(methylthio)thiocarbonyl-α-D-rhamnopyranoside

methyl 2,4-di-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

(2S,3S,5S,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-ol