methyl 2-desoxy-2,4-di-C-methyl-3-O-benzyl-5-methoxycarbonyl-Δ^4,5-α-L-threopentapyranoside

Base Information

• Chemical Name: methyl 2-desoxy-2,4-di-C-methyl-3-O-benzyl-5-methoxycarbonyl-Δ^4,5-α-L-threopentapyranoside
• CAS No.: 81196-18-1
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359

Synonyms:methyl 2-desoxy-2,4-di-C-methyl-3-O-benzyl-5-methoxycarbonyl-Δ^4,5-α-L-threopentapyranoside

Chemical Property of methyl 2-desoxy-2,4-di-C-methyl-3-O-benzyl-5-methoxycarbonyl-Δ^4,5-α-L-threopentapyranoside

Chemical Property:

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Technology Process of methyl 2-desoxy-2,4-di-C-methyl-3-O-benzyl-5-methoxycarbonyl-Δ^4,5-α-L-threopentapyranoside

There total 12 articles about methyl 2-desoxy-2,4-di-C-methyl-3-O-benzyl-5-methoxycarbonyl-Δ^4,5-α-L-threopentapyranoside 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: 89.0%

methanol (67-56-1) + methyl 2-desoxy-2,4-di-C-methyl-3-O-benzyl-6-oxo-α-L-threopentapyranoside (81186-83-6) → methyl 2-desoxy-2,4-di-C-methyl-3-O-benzyl-5-methoxycarbonyl-Δ4,5-α-L-threopentapyranoside (81196-18-1)

Guidance literature:

With potassium cyanide; manganese(IV) oxide; In acetic acid;

DOI:10.1016/S0040-4039(01)82944-0

Reference yield:

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose (33208-47-8) → methyl 2-desoxy-2,4-di-C-methyl-3-O-benzyl-5-methoxycarbonyl-Δ4,5-α-L-threopentapyranoside (81196-18-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / diethyl ether / 12 h / Heating

2: 2.) Hydrogen / 5percent Pd/C / 1.) pyridine 2.) methanol

3: 96 percent / DMSO, (COCl)2

4: 98 percent / 1 h / Heating

5: 96 percent / NaH / dimethylformamide

6: 20percent HCl / 4 h / 20 °C

7: 3percent HCl / methanol / 20 °C

8: 98 percent / DMSO, (COCl)2

9: 98 percent / Ca(OH)2 / methanol / Heating

10: 89 percent / KCN, MnO₂ / acetic acid

With hydrogenchloride; potassium cyanide; manganese(IV) oxide; calcium hydroxide; oxalyl dichloride; hydrogen; sodium hydride; dimethyl sulfoxide; palladium on activated charcoal; In methanol; diethyl ether; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)82944-0

Reference yield:

4-O-benzyl-2-methyl-1,6-anhydro-β-D-glucopyranose (65190-43-4) → methyl 2-desoxy-2,4-di-C-methyl-3-O-benzyl-5-methoxycarbonyl-Δ4,5-α-L-threopentapyranoside (81196-18-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 2.) Hydrogen / 5percent Pd/C / 1.) pyridine 2.) methanol

2: 96 percent / DMSO, (COCl)2

3: 98 percent / 1 h / Heating

4: 96 percent / NaH / dimethylformamide

5: 20percent HCl / 4 h / 20 °C

6: 3percent HCl / methanol / 20 °C

7: 98 percent / DMSO, (COCl)2

8: 98 percent / Ca(OH)2 / methanol / Heating

9: 89 percent / KCN, MnO₂ / acetic acid

With hydrogenchloride; potassium cyanide; manganese(IV) oxide; calcium hydroxide; oxalyl dichloride; hydrogen; sodium hydride; dimethyl sulfoxide; palladium on activated charcoal; In methanol; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)82944-0

upstream raw materials:

methanol

methyl 2-desoxy-2,4-di-C-methyl-3-O-benzyl-6-oxo-α-L-threopentapyranoside

1,6-anhydro-2-desoxy-2,4-di-C-methyl-β-D-galactopyranose

1,6-anhydro-2-desoxy-2,4-di-C-methyl-3,4-di-O-benzyl-β-D-galactopyranose

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