Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-{(2S,3R,4S,5R,6R)-4-[(2S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-5-hydroxy-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy}-3,4-dihydro-2H-pyran-2-ylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-{(2S,3R,4S,5R,6R)-4-[(2S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-5-hydroxy-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy}-3,4-dihydro-2H-pyran-2-ylmethyl ester
CAS No.:370094-62-5
Molecular Formula:C₃₈H₅₅IO₁₁SSi
Molecular Weight:874.904
Hs Code.:

Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-{(2S,3R,4S,5R,6R)-4-[(2S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-5-hydroxy-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy}-3,4-dihydro-2H-pyran-2-ylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-{(2S,3R,4S,5R,6R)-4-[(2S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-5-hydroxy-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy}-3,4-dihydro-2H-pyran-2-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-{(2S,3R,4S,5R,6R)-4-[(2S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-5-hydroxy-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy}-3,4-dihydro-2H-pyran-2-ylmethyl ester

There total 11 articles about Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-{(2S,3R,4S,5R,6R)-4-[(2S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-5-hydroxy-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy}-3,4-dihydro-2H-pyran-2-ylmethyl ester 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:

: 288859-46-1
1-O-acetyl-4-O-(tert-butyldimethyl)silyl-β-L-rhodinose

: 370094-61-4
Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-((2S,3R,4S,5S,6R)-4,5-dihydroxy-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-2-ylmethyl ester

: 370094-63-6
Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-{(2S,3R,4S,5S,6R)-5-[(2S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-4-hydroxy-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy}-3,4-dihydro-2H-pyran-2-ylmethyl ester

: 370094-62-5
Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-{(2S,3R,4S,5R,6R)-4-[(2S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-5-hydroxy-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy}-3,4-dihydro-2H-pyran-2-ylmethyl ester

Guidance literature:: With triethylsilyl trifluoromethyl sulfonate; In diethyl ether; at -78 ℃; for 0.25h;
DOI:10.1021/jo015756a

Reference yield:

: 854608-80-3
(4S,5S)-4-O-(tert-butyldimethylsilyl)-2,3,6-trideoxy-hexopyranose

: 370094-62-5
Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-{(2S,3R,4S,5R,6R)-4-[(2S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-5-hydroxy-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy}-3,4-dihydro-2H-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 9.2 g / Et₃N / CH₂Cl₂ / 7.5 h / 0 - 23 °C

2: (C₂H₅)3SiOSO₂CF₃ / diethyl ether / 0.25 h / -78 °C

With triethylsilyl trifluoromethyl sulfonate; triethylamine; In diethyl ether; dichloromethane;
DOI:10.1021/jo015756a

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 370094-62-5
Toluene-4-sulfonic acid (2R,3S,4R)-4-benzyloxy-3-{(2S,3R,4S,5R,6R)-4-[(2S,5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-5-hydroxy-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy}-3,4-dihydro-2H-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 53.4 g / imidazole / dimethylformamide / 12.5 h / 23 °C

2.1: catecholborane; (Ph₃P)3RhCl / tetrahydrofuran / 1.17 h

2.2: 88 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; ethanol / 0.25 h

3.1: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 1.17 h / -78 - 0 °C

4.1: DDQ / CH₂Cl₂; H₂O / 0.75 h / 23 °C / pH 7

5.1: 9.2 g / Et₃N / CH₂Cl₂ / 7.5 h / 0 - 23 °C

6.1: (C₂H₅)3SiOSO₂CF₃ / diethyl ether / 0.25 h / -78 °C

With 1H-imidazole; Wilkinson's catalyst; oxalyl dichloride; triethylsilyl trifluoromethyl sulfonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; benzo[1,3,2]dioxaborole; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 3.1: Swern oxidation;
DOI:10.1021/jo015756a