3-O-benzyl-5,6-dideoxy-5-C-(1',4'-dimethoxynaphthalen-2'-yl)-1,2-O-isopropylidene-6-nitro-β-L-idofuranose

Base Information

Chemical Name:3-O-benzyl-5,6-dideoxy-5-C-(1',4'-dimethoxynaphthalen-2'-yl)-1,2-O-isopropylidene-6-nitro-β-L-idofuranose
CAS No.:847984-53-6
Molecular Formula:C₂₈H₃₁NO₈
Molecular Weight:509.556
Hs Code.:

Synonyms:3-O-benzyl-5,6-dideoxy-5-C-(1',4'-dimethoxynaphthalen-2'-yl)-1,2-O-isopropylidene-6-nitro-β-L-idofuranose

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Chemical Property of 3-O-benzyl-5,6-dideoxy-5-C-(1',4'-dimethoxynaphthalen-2'-yl)-1,2-O-isopropylidene-6-nitro-β-L-idofuranose

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Technology Process of 3-O-benzyl-5,6-dideoxy-5-C-(1',4'-dimethoxynaphthalen-2'-yl)-1,2-O-isopropylidene-6-nitro-β-L-idofuranose

There total 2 articles about 3-O-benzyl-5,6-dideoxy-5-C-(1',4'-dimethoxynaphthalen-2'-yl)-1,2-O-isopropylidene-6-nitro-β-L-idofuranose 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: 54.0%

: 69177-83-9,78283-50-8,86495-59-2,114181-97-4,141782-01-6,51173-35-4
3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-α-D-xylo-hex-5-enofuranose

: 64648-81-3
2-bromo-1,4-dimethoxynaphthalene

: 847984-53-6
3-O-benzyl-5,6-dideoxy-5-C-(1',4'-dimethoxynaphthalen-2'-yl)-1,2-O-isopropylidene-6-nitro-β-L-idofuranose

: (3aR,5R,6S,6aR)-6-Benzyloxy-5-[(R)-1-(1,4-dimethoxy-naphthalen-2-yl)-2-nitro-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: 2-bromo-1,4-dimethoxynaphthalene; With tert.-butyl lithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h; Inert atmosphere;

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-α-D-xylo-hex-5-enofuranose; In tetrahydrofuran; hexane; at -78 ℃; for 4h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; hexane; water; optical yield given as %de; diastereoselective reaction;
DOI:10.1016/j.tet.2011.11.072

Reference yield:

: 64648-81-3
2-bromo-1,4-dimethoxynaphthalene

: 86495-59-2
(E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-α-D-xylo-hex-5-eno-1,4-furanose

: 847984-53-6
3-O-benzyl-5,6-dideoxy-5-C-(1',4'-dimethoxynaphthalen-2'-yl)-1,2-O-isopropylidene-6-nitro-β-L-idofuranose

: (3aR,5R,6S,6aR)-6-Benzyloxy-5-[(R)-1-(1,4-dimethoxy-naphthalen-2-yl)-2-nitro-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: 2-bromo-1,4-dimethoxynaphthalene; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 0.25h;

(E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-α-D-xylo-hex-5-eno-1,4-furanose; In tetrahydrofuran; at -78 ℃; for 4h;
DOI:10.1016/j.tetasy.2004.11.045