methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-β-L-xylo-hexopyranoside

Base Information

• Chemical Name: methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-β-L-xylo-hexopyranoside
• CAS No.: 268203-12-9
• Molecular Formula: C₂₂H₂₈O₄
• Molecular Weight: 356.462
• Mol file: 268203-12-9.mol

Synonyms:methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-β-L-xylo-hexopyranoside

Chemical Property of methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-β-L-xylo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-β-L-xylo-hexopyranoside

There total 12 articles about methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-β-L-xylo-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: 92.0%

benzyl chloride (100-44-7) + methyl 3-O-benzyl-2,6-dideoxy-3-C-methyl-β-L-xylo-hexopyranoside (268203-11-8) → methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-β-L-xylo-hexopyranoside (268203-12-9)

Guidance literature:

With potassium hydroxide; at 120 - 130 ℃; for 1.5h;

DOI:10.1016/S0957-4166(99)00563-7

Reference yield:

methyl 2-deoxy-5-O-trityl-β-D-glycero-pentofuranosid-3-ulose (51921-34-7) → methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-β-L-xylo-hexopyranoside (268203-12-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 68 percent / CeCl₃ / tetrahydrofuran; diethyl ether / 2 h / -78 - 0 °C

2: 87 percent / KOH / 2 h / 130 - 140 °C

3: Amberlyst-15 macroreticular resin (strongly acidic) / methanol / 8 h / 20 °C

4: DMSO; trifluoroacetic anhydride; Et₃N / CH₂Cl₂ / 1 h / -78 - 20 °C

5: 27 percent / diethyl ether; tetrahydrofuran / 1 h / 20 °C

6: 41 percent / HCl / methanol; diethyl ether / 3 h / 50 °C

7: 92 percent / KOH / 1.5 h / 120 - 130 °C

With hydrogenchloride; potassium hydroxide; cerium(III) chloride; Amberlyst-15 macroreticular resin (strongly acidic); dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1: Methylation / 2: benzylation / 3: detritylation / 4: Oxidation / 5: Methylation / 6: Rearrangement / 7: benzylation;

DOI:10.1016/S0957-4166(99)00563-7

Reference yield:

methyl 2-deoxy-5-O-trityl-α-D-glycero-pentofuranosid-3-ulose (51885-24-6) → methyl 3,4-di-O-benzyl-2,6-dideoxy-3-C-methyl-β-L-xylo-hexopyranoside (268203-12-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 78 percent / CeCl₃ / tetrahydrofuran; diethyl ether / 2 h / -78 - 0 °C

2: 70 percent / KOH / 2 h / 130 - 140 °C

3: Amberlyst-15 macroreticular resin (strongly acidic) / methanol / 8 h / 20 °C

4: DMSO; trifluoroacetic anhydride; Et₃N / CH₂Cl₂ / 1 h / -78 - 20 °C

5: 27 percent / diethyl ether; tetrahydrofuran / 1 h / 20 °C

6: 41 percent / HCl / methanol; diethyl ether / 3 h / 50 °C

7: 92 percent / KOH / 1.5 h / 120 - 130 °C

With hydrogenchloride; potassium hydroxide; cerium(III) chloride; Amberlyst-15 macroreticular resin (strongly acidic); dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1: Methylation / 2: benzylation / 3: detritylation / 4: Oxidation / 5: Methylation / 6: Rearrangement / 7: benzylation;

DOI:10.1016/S0957-4166(99)00563-7

upstream raw materials:

benzyl chloride

methyl 3-O-benzyl-2,6-dideoxy-3-C-methyl-β-L-xylo-hexopyranoside

methyl 2-deoxy-5-O-trityl-α-D-glycero-pentofuranosid-3-ulose

methyl 2-deoxy-5-O-trityl-β-D-glycero-pentofuranosid-3-ulose