methyl 3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-1-phenylthio-2-ulos-β-D-glucuronate

Base Information

Chemical Name:methyl 3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-1-phenylthio-2-ulos-β-D-glucuronate
CAS No.:252001-18-6
Molecular Formula:C₂₅H₄₀O₇SSi₂
Molecular Weight:540.825
Hs Code.:

Synonyms:methyl 3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-1-phenylthio-2-ulos-β-D-glucuronate

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Chemical Property of methyl 3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-1-phenylthio-2-ulos-β-D-glucuronate

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Technology Process of methyl 3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-1-phenylthio-2-ulos-β-D-glucuronate

There total 8 articles about methyl 3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-1-phenylthio-2-ulos-β-D-glucuronate 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:

: 252001-17-5
(1S,3S,4R,4aR,9aR)-4-Hydroxy-6,6,8,8-tetraisopropyl-3-phenylsulfanyl-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester

: 252001-18-6
methyl 3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-1-phenylthio-2-ulos-β-D-glucuronate

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1021/ja992608h

Reference yield:

: 69304-37-6
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

: 252001-18-6
methyl 3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-1-phenylthio-2-ulos-β-D-glucuronate

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridine

1.2: 59 percent / p-TsOH / dimethylformamide

2.1: pyridine

4.1: TFA / CH₂Cl₂

5.1: DCC; DMSO; TFA / dimethylsulfoxide

5.2: 61 percent / PDC / dimethylformamide

6.1: K₂CO₃ / methanol

7.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂

With pyridine; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane; dimethyl sulfoxide; 1.1: silylation / 1.2: Isomerization / 2.1: Etherification / 3.1: Acetylation / 4.1: deprotection / 5.1: Moffatt oxidation / 5.2: Oxidation / 6.1: Hydrolysis / 7.1: Swern oxidation;
DOI:10.1021/ja992608h

Reference yield:

: 2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1
(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 252001-18-6
methyl 3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-1-phenylthio-2-ulos-β-D-glucuronate

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridine

1.2: 59 percent / p-TsOH / dimethylformamide

2.1: pyridine

4.1: TFA / CH₂Cl₂

5.1: DCC; DMSO; TFA / dimethylsulfoxide

5.2: 61 percent / PDC / dimethylformamide

6.1: K₂CO₃ / methanol

7.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂

With pyridine; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane; dimethyl sulfoxide; 1.1: silylation / 1.2: Isomerization / 2.1: Etherification / 3.1: Acetylation / 4.1: deprotection / 5.1: Moffatt oxidation / 5.2: Oxidation / 6.1: Hydrolysis / 7.1: Swern oxidation;
DOI:10.1021/ja992608h