ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-6-O-(3'-methanesulfonyloxypropyl)-1-thio-β-D-galactopyranoside

Base Information

Chemical Name:ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-6-O-(3'-methanesulfonyloxypropyl)-1-thio-β-D-galactopyranoside
CAS No.:257286-43-4
Molecular Formula:C₂₃H₃₆O₉S₂
Molecular Weight:520.665
Hs Code.:

Synonyms:ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-6-O-(3'-methanesulfonyloxypropyl)-1-thio-β-D-galactopyranoside

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Chemical Property of ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-6-O-(3'-methanesulfonyloxypropyl)-1-thio-β-D-galactopyranoside

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Technology Process of ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-6-O-(3'-methanesulfonyloxypropyl)-1-thio-β-D-galactopyranoside

There total 6 articles about ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-6-O-(3'-methanesulfonyloxypropyl)-1-thio-β-D-galactopyranoside 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: 93.0%

: 124-63-0
methanesulfonyl chloride

: 257286-42-3
ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-6-O-(3'-hydroxypropyl)-1-thio-β-D-galactopyranoside

: 257286-43-4
ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-6-O-(3'-methanesulfonyloxypropyl)-1-thio-β-D-galactopyranoside

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo990979a

Reference yield:

: 206857-11-6
ethyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-1-thio-β-D-galactopyranoside

: 257286-43-4
ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-6-O-(3'-methanesulfonyloxypropyl)-1-thio-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: NaH / dimethylformamide / 4 h

2: HCl / H₂O; CH₂Cl₂

3: 91 percent / NaH / tetrahydrofuran / 3 h / 60 °C

4: 100 percent / TBAF / tetrahydrofuran / 1 h

5: 93 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

With hydrogenchloride; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1: Alkylation / 2: Hydrolysis / 3: Substitution / 4: desilylation / 5: Substitution;
DOI:10.1021/jo990979a

Reference yield:

: 56245-60-4,686299-00-3
ethyl 1-thio-β-D-galactopyranoside

: 257286-43-4
ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-6-O-(3'-methanesulfonyloxypropyl)-1-thio-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: TsOH

2: NaH / dimethylformamide / 4 h

3: HCl / H₂O; CH₂Cl₂

4: 91 percent / NaH / tetrahydrofuran / 3 h / 60 °C

5: 100 percent / TBAF / tetrahydrofuran / 1 h

6: 93 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

With hydrogenchloride; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1: Substitution / 2: Alkylation / 3: Hydrolysis / 4: Substitution / 5: desilylation / 6: Substitution;
DOI:10.1021/jo990979a