1,5-anhydro-2,4,6-trideoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4-<(2,4-dinitrophenyl)thio>-D-ribo-hex-1-enopyranose

Base Information

Chemical Name:1,5-anhydro-2,4,6-trideoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4-<(2,4-dinitrophenyl)thio>-D-ribo-hex-1-enopyranose
CAS No.:134262-68-3
Molecular Formula:C₁₈H₂₆N₂O₆SSi
Molecular Weight:426.566
Hs Code.:

Synonyms:1,5-anhydro-2,4,6-trideoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4-<(2,4-dinitrophenyl)thio>-D-ribo-hex-1-enopyranose

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Chemical Property of 1,5-anhydro-2,4,6-trideoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4-<(2,4-dinitrophenyl)thio>-D-ribo-hex-1-enopyranose

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Technology Process of 1,5-anhydro-2,4,6-trideoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4-<(2,4-dinitrophenyl)thio>-D-ribo-hex-1-enopyranose

There total 11 articles about 1,5-anhydro-2,4,6-trideoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4-<(2,4-dinitrophenyl)thio>-D-ribo-hex-1-enopyranose 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: 88.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 134262-67-2
1,5-anhydro-2,4,6-trideoxy-4-<(2,4-dinitrophenyl)thio>-D-ribo-hex-1-enopyranose

: 134262-68-3
1,5-anhydro-2,4,6-trideoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4-<(2,4-dinitrophenyl)thio>-D-ribo-hex-1-enopyranose

Guidance literature:: With pyridine; In dichloromethane; for 48h; Ambient temperature;
DOI:10.1021/ja00126a013

Reference yield:

: 125848-19-3,286410-13-7
phenyl-2,4-di-O-acetyl-2,3-dideoxy-1-thio-α-D-threo-hex-2-eno-pyranoside

: 134262-68-3
1,5-anhydro-2,4,6-trideoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4-<(2,4-dinitrophenyl)thio>-D-ribo-hex-1-enopyranose

Guidance literature:: Multi-step reaction with 7 steps

1: NaOMe / methanol

2: 86 percent / TBAB / CH₂Cl₂

3: 91 percent / LAH / tetrahydrofuran

4: 1.) MsCl, Et₃N / 2.) DMF

5: 1.) LAH / 1.) THF

6: 1.) m-CBA, 2.) Et₂NH / 1.) CH₂Cl₂, 2.) THF

7: pyridine / CH₂Cl₂

With pyridine; lithium aluminium tetrahydride; m-formylphenyl benzoic acid; tetrabutylammomium bromide; sodium methylate; methanesulfonyl chloride; diethylamine; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo951560x

Reference yield:

: 135726-16-8
phenyl 2,3,6-trideoxy-1-thio-α-D-threo-hex-2-enopyranoside

: 134262-68-3
1,5-anhydro-2,4,6-trideoxy-3-O-<(1,1-dimethylethyl)dimethylsilyl>-4-<(2,4-dinitrophenyl)thio>-D-ribo-hex-1-enopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) MsCl, Et₃N / 2.) DMF

2: 1.) LAH / 1.) THF

3: 1.) m-CBA, 2.) Et₂NH / 1.) CH₂Cl₂, 2.) THF

4: pyridine / CH₂Cl₂

With pyridine; lithium aluminium tetrahydride; m-formylphenyl benzoic acid; methanesulfonyl chloride; diethylamine; triethylamine; In dichloromethane;
DOI:10.1021/jo951560x