6-O-(p-tert-butyldimethylsilyloxyphenylsulfonyl)-1,2-O-isopropylidene-3-O-methyl-5-O-(prop-1'-enyl)-α-D-glucofuranose

Base Information

Chemical Name:6-O-(p-tert-butyldimethylsilyloxyphenylsulfonyl)-1,2-O-isopropylidene-3-O-methyl-5-O-(prop-1'-enyl)-α-D-glucofuranose
CAS No.:473734-82-6
Molecular Formula:C₂₅H₄₀O₉SSi
Molecular Weight:544.739
Hs Code.:

Synonyms:6-O-(p-tert-butyldimethylsilyloxyphenylsulfonyl)-1,2-O-isopropylidene-3-O-methyl-5-O-(prop-1'-enyl)-α-D-glucofuranose

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Chemical Property of 6-O-(p-tert-butyldimethylsilyloxyphenylsulfonyl)-1,2-O-isopropylidene-3-O-methyl-5-O-(prop-1'-enyl)-α-D-glucofuranose

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Technology Process of 6-O-(p-tert-butyldimethylsilyloxyphenylsulfonyl)-1,2-O-isopropylidene-3-O-methyl-5-O-(prop-1'-enyl)-α-D-glucofuranose

There total 5 articles about 6-O-(p-tert-butyldimethylsilyloxyphenylsulfonyl)-1,2-O-isopropylidene-3-O-methyl-5-O-(prop-1'-enyl)-α-D-glucofuranose 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: 86.0%

: 473734-75-7
6-O-(p-hydroxyphenylsulfonyl)-1,2-O-isopropylidene-3-O-methyl-5-O-(prop-1'-enyl)-α-D-glucofuranose

: 18162-48-6
tert-butyldimethylsilyl chloride

: 473734-82-6
6-O-(p-tert-butyldimethylsilyloxyphenylsulfonyl)-1,2-O-isopropylidene-3-O-methyl-5-O-(prop-1'-enyl)-α-D-glucofuranose

Guidance literature:: With 1H-imidazole; In acetonitrile; at 20 ℃; for 2h;
DOI:10.1002/1099-0690(200207)2002:14<2377::AID-EJOC2377>3.0.CO;2-I

Reference yield:

: 51213-03-7
(1R)-1-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(trityloxy)ethan-1-ol

: 473734-82-6
6-O-(p-tert-butyldimethylsilyloxyphenylsulfonyl)-1,2-O-isopropylidene-3-O-methyl-5-O-(prop-1'-enyl)-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / NaH / dimethylformamide

2: 92 percent / p-TsOH / methanol / 2 h / 20 °C

3: 93 percent / t-BuOK / dimethylsulfoxide / 0.67 h / 50 °C

4: 74 percent / pyridine; DMAP

5: 86 percent / sodium; MeOH / 2 h / 20 °C

6: 86 percent / imidazole / acetonitrile / 2 h / 20 °C

With pyridine; 1H-imidazole; methanol; dmap; potassium tert-butylate; sodium; sodium hydride; toluene-4-sulfonic acid; In methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/1099-0690(200207)2002:14<2377::AID-EJOC2377>3.0.CO;2-I

Reference yield:

: 89821-70-5
5-O-allyl-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose

: 473734-82-6
6-O-(p-tert-butyldimethylsilyloxyphenylsulfonyl)-1,2-O-isopropylidene-3-O-methyl-5-O-(prop-1'-enyl)-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / t-BuOK / dimethylsulfoxide / 0.67 h / 50 °C

2: 74 percent / pyridine; DMAP

3: 86 percent / sodium; MeOH / 2 h / 20 °C

4: 86 percent / imidazole / acetonitrile / 2 h / 20 °C

With pyridine; 1H-imidazole; methanol; dmap; potassium tert-butylate; sodium; In dimethyl sulfoxide; acetonitrile;
DOI:10.1002/1099-0690(200207)2002:14<2377::AID-EJOC2377>3.0.CO;2-I