methyl 5-(acetoxyamino)-N-benzyl-5-deoxy-2,3-isopropylidene-5-(2-furyl)-β-D-allo-1,4-pentofuranoside

Base Information

• Chemical Name: methyl 5-(acetoxyamino)-N-benzyl-5-deoxy-2,3-isopropylidene-5-(2-furyl)-β-D-allo-1,4-pentofuranoside
• CAS No.: 191997-67-8
• Molecular Formula: C₂₂H₂₇NO₇
• Molecular Weight: 417.459

Synonyms:methyl 5-(acetoxyamino)-N-benzyl-5-deoxy-2,3-isopropylidene-5-(2-furyl)-β-D-allo-1,4-pentofuranoside

Chemical Property of methyl 5-(acetoxyamino)-N-benzyl-5-deoxy-2,3-isopropylidene-5-(2-furyl)-β-D-allo-1,4-pentofuranoside

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Technology Process of methyl 5-(acetoxyamino)-N-benzyl-5-deoxy-2,3-isopropylidene-5-(2-furyl)-β-D-allo-1,4-pentofuranoside

There total 2 articles about methyl 5-(acetoxyamino)-N-benzyl-5-deoxy-2,3-isopropylidene-5-(2-furyl)-β-D-allo-1,4-pentofuranoside 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: 100.0%

acetic anhydride (108-24-7) + N-Benzyl-N-[(S)-furan-2-yl-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methyl]-hydroxylamine (161614-80-8) → methyl 5-(acetoxyamino)-N-benzyl-5-deoxy-2,3-isopropylidene-5-(2-furyl)-β-D-allo-1,4-pentofuranoside (191997-67-8)

Guidance literature:

With dmap; In pyridine; for 2h; Ambient temperature;

DOI:10.1021/jo9702913

Reference yield:

(Z)-N-(5-deoxy-2,3-O-isopropylidene-1-O-methyl-β-D-ribo-1,4-furanose-5-ylidene)benzylamine N-oxide (161614-79-5,191997-34-9) → methyl 5-(acetoxyamino)-N-benzyl-5-deoxy-2,3-isopropylidene-5-(2-furyl)-β-D-allo-1,4-pentofuranoside (191997-67-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / Et₂AlCl / hexane; diethyl ether; tetrahydrofuran / 2 h / -80 °C

2: 100 percent / DMAP / pyridine / 2 h / Ambient temperature

With dmap; diethylaluminium chloride; In tetrahydrofuran; pyridine; diethyl ether; hexane;

DOI:10.1021/jo9702913

Reference yield: 36.0%

acetic anhydride (108-24-7) + methyl 5-(acetoxyamino)-N-benzyl-5-deoxy-2,3-isopropylidene-5-(2-furyl)-β-D-allo-1,4-pentofuranoside (191997-67-8) → 5-(acetoxyamino)-N-benzyl-5-deoxy-5-(2-furyl)-1,2,3-tri-O-acetyl-α-D-allo-1,4-pentofuranoside + 5-(acetoxyamino)-N-benzyl-5-deoxy-5-(2-furyl)-1,2,3-tri-O-acetyl-β-D-allo-1,4-pentofuranoside

Guidance literature:

With hydrogenchloride; In acetic acid; at 70 ℃; for 4h;

DOI:10.1021/jo9702913

upstream raw materials:

acetic anhydride

N-Benzyl-N-[(S)-furan-2-yl-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methyl]-hydroxylamine

(Z)-N-(5-deoxy-2,3-O-isopropylidene-1-O-methyl-β-D-ribo-1,4-furanose-5-ylidene)benzylamine N-oxide

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