4-benzylamino-1,2,3,4,7,8-hexadeoxy-5,6-O-isopropylidene-D-ribo-oct-1,7-dienitol

Base Information

• Chemical Name: 4-benzylamino-1,2,3,4,7,8-hexadeoxy-5,6-O-isopropylidene-D-ribo-oct-1,7-dienitol
• CAS No.: 301523-39-7
• Molecular Formula: C₁₈H₂₅NO₂
• Molecular Weight: 287.402

Synonyms:4-benzylamino-1,2,3,4,7,8-hexadeoxy-5,6-O-isopropylidene-D-ribo-oct-1,7-dienitol

Chemical Property of 4-benzylamino-1,2,3,4,7,8-hexadeoxy-5,6-O-isopropylidene-D-ribo-oct-1,7-dienitol

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Technology Process of 4-benzylamino-1,2,3,4,7,8-hexadeoxy-5,6-O-isopropylidene-D-ribo-oct-1,7-dienitol

There total 9 articles about 4-benzylamino-1,2,3,4,7,8-hexadeoxy-5,6-O-isopropylidene-D-ribo-oct-1,7-dienitol 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: 85.0%

(4S,5S,6R)-4-[(N-benzyl)amino]-5,6-(isopropylidenedioxy)-7-octen-1-yne (444883-30-1) → 4-benzylamino-1,2,3,4,7,8-hexadeoxy-5,6-O-isopropylidene-D-ribo-oct-1,7-dienitol (301523-39-7)

Guidance literature:

With hydrogen; acetic acid; Lindlar's catalyst; In ethanol;

DOI:10.1021/jo0200062

Reference yield: 70.0%

methyl 5-deoxy-5-iodo-2,3-isopropylidene-β-D-ribofuranoside (38838-06-1) + allyl bromide (106-95-6) + benzylamine (100-46-9) → 4-benzylamino-1,2,3,4,7,8-hexadeoxy-5,6-O-isopropylidene-D-ribo-oct-1,7-dienitol (301523-39-7) + Benzyl-[(R)-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-amine

Guidance literature:

With zinc; In tetrahydrofuran; water; at 40 ℃; for 2h; sonication;

DOI:10.1021/ja001415n

Reference yield: 70.0%

methyl 5-deoxy-5-iodo-2,3-isopropylidene-β-D-ribofuranoside (38838-06-1) + allyl bromide (106-95-6) + benzylamine (100-46-9) → 4-benzylamino-1,2,3,4,7,8-hexadeoxy-5,6-O-isopropylidene-D-ribo-oct-1,7-dienitol (301523-39-7)

Guidance literature:

With zinc; In tetrahydrofuran; sonication;

DOI:10.1016/S0040-4039(02)01364-3

upstream raw materials:

methyl 5-deoxy-5-iodo-2,3-isopropylidene-β-D-ribofuranoside

allyl bromide

benzylamine

(4S,5S,6R)-4-[(N-benzyl)amino]-5,6-(isopropylidenedioxy)-7-octen-1-yne

Downstream raw materials:

(3R,4S,5S)-3,4-O-isopropylidene-5-(N-benzyl)-o-nitro-benzensulfon-amino-octa-1,7-diene-3,4-diol

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