(2R,3aS,4R,5R,6aS)-2-(azidomethyl)-4-benzyloxy-5-(benzyloxymethyl)hexahydrofuro[3,2-b]furan

Base Information

Chemical Name:(2R,3aS,4R,5R,6aS)-2-(azidomethyl)-4-benzyloxy-5-(benzyloxymethyl)hexahydrofuro[3,2-b]furan
CAS No.:326487-11-0
Molecular Formula:C₂₂H₂₅N₃O₄
Molecular Weight:395.458
Hs Code.:

Synonyms:(2R,3aS,4R,5R,6aS)-2-(azidomethyl)-4-benzyloxy-5-(benzyloxymethyl)hexahydrofuro[3,2-b]furan

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Chemical Property of (2R,3aS,4R,5R,6aS)-2-(azidomethyl)-4-benzyloxy-5-(benzyloxymethyl)hexahydrofuro[3,2-b]furan

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Technology Process of (2R,3aS,4R,5R,6aS)-2-(azidomethyl)-4-benzyloxy-5-(benzyloxymethyl)hexahydrofuro[3,2-b]furan

There total 4 articles about (2R,3aS,4R,5R,6aS)-2-(azidomethyl)-4-benzyloxy-5-(benzyloxymethyl)hexahydrofuro[3,2-b]furan 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: 40.0%

: (2RS,4aS,5R,6R,6aR)-2-iodomethyl-6-benzyloxy-5-(benzyloxymethyl)hexahydrofuro[3,2-b]furan

: 326487-12-1
(2S,3aS,4R,5R,6aS)-2-(azidomethyl)-4-benzyloxy-5-(benzyloxymethyl)hexahydrofuro[3,2-b]furan

: 326487-11-0
(2R,3aS,4R,5R,6aS)-2-(azidomethyl)-4-benzyloxy-5-(benzyloxymethyl)hexahydrofuro[3,2-b]furan

Guidance literature:: With tetrabutylammoniun azide; at 70 ℃; for 24h;
DOI:10.1039/b110453e

Reference yield:

: (2RS,3aS,4R,5R,6aS)-2-(azidomethyl)-4-hydroxy-5-(hydroxymethyl)hexahydrofuro[3,2-b]furan

: 100-39-0
benzyl bromide

: 326487-12-1
(2S,3aS,4R,5R,6aS)-2-(azidomethyl)-4-benzyloxy-5-(benzyloxymethyl)hexahydrofuro[3,2-b]furan

: 326487-11-0
(2R,3aS,4R,5R,6aS)-2-(azidomethyl)-4-benzyloxy-5-(benzyloxymethyl)hexahydrofuro[3,2-b]furan

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h; Title compound not separated from byproducts;
DOI:10.1002/ejoc.200600132

Reference yield:

: 62255-44-1
1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose

: 326487-11-0
(2R,3aS,4R,5R,6aS)-2-(azidomethyl)-4-benzyloxy-5-(benzyloxymethyl)hexahydrofuro[3,2-b]furan

Guidance literature:: Multi-step reaction with 3 steps

1: 75 percent / BF₃*Et₂O / acetonitrile / 1.5 h / 20 °C

2: 0.185 g / NIS / tetrahydrofuran / 144 h / 20 °C

3: 40 percent / tetrabutylammonium azide / 24 h / 70 °C

With N-iodo-succinimide; boron trifluoride diethyl etherate; tetrabutylammoniun azide; In tetrahydrofuran; acetonitrile;
DOI:10.1039/b110453e