3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-5-deoxy-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-D-ribofuranose

Base Information

Chemical Name:3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-5-deoxy-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-D-ribofuranose
CAS No.:912567-58-9
Molecular Formula:C₃₅H₄₅F₃O₁₄S
Molecular Weight:778.795
Hs Code.:

3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-5-deoxy-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-D-ribofuranose

Synonyms:3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-5-deoxy-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-D-ribofuranose

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Chemical Property of 3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-5-deoxy-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-D-ribofuranose

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Technology Process of 3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-5-deoxy-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-D-ribofuranose

There total 4 articles about 3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-5-deoxy-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-D-ribofuranose 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: 90.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 295320-98-8
3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose

: 912567-58-9
3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-5-deoxy-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-D-ribofuranose

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1021/jm060310d

Reference yield:

: 518332-41-7
2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-phenylsulfinyl-β-D-glucopyranoside

: 912567-58-9
3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-5-deoxy-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 3 steps

1: 78 percent / 2,6-di-tert-butyl-4-methylpyridine / diethyl ether / 8 h / -78 °C

2: 82 percent / TBAF / tetrahydrofuran / 20 °C

3: 90 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1 h / -78 °C

With 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jm060310d

Reference yield:

: 196868-07-2
1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-ribofuranoside

: 912567-58-9
3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-α-D-glucopyranosyl]-5-deoxy-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 3 steps

1: 78 percent / 2,6-di-tert-butyl-4-methylpyridine / diethyl ether / 8 h / -78 °C

2: 82 percent / TBAF / tetrahydrofuran / 20 °C

3: 90 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1 h / -78 °C

With 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jm060310d