ethyl 7-O-benzyl-2,3-O-isopropylidene-4-O-p-methoxybenzyl-1-thio-D-glycero-α-D-manno-heptopyranoside

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Chemical Name:ethyl 7-O-benzyl-2,3-O-isopropylidene-4-O-p-methoxybenzyl-1-thio-D-glycero-α-D-manno-heptopyranoside
CAS No.:286845-66-7
Molecular Formula:C₂₇H₃₆O₇S
Molecular Weight:504.645
Hs Code.:

Synonyms:ethyl 7-O-benzyl-2,3-O-isopropylidene-4-O-p-methoxybenzyl-1-thio-D-glycero-α-D-manno-heptopyranoside

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Chemical Property of ethyl 7-O-benzyl-2,3-O-isopropylidene-4-O-p-methoxybenzyl-1-thio-D-glycero-α-D-manno-heptopyranoside

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Technology Process of ethyl 7-O-benzyl-2,3-O-isopropylidene-4-O-p-methoxybenzyl-1-thio-D-glycero-α-D-manno-heptopyranoside

There total 7 articles about ethyl 7-O-benzyl-2,3-O-isopropylidene-4-O-p-methoxybenzyl-1-thio-D-glycero-α-D-manno-heptopyranoside 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: 21.0%

: 3587-60-8
Benzyloxymethyl chloride

: (3aS,4R,6S,7S,7aS)-4-Ethylsulfanyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carbaldehyde

: 286845-66-7
ethyl 7-O-benzyl-2,3-O-isopropylidene-4-O-p-methoxybenzyl-1-thio-D-glycero-α-D-manno-heptopyranoside

: 286845-67-8
ethyl 7-O-benzyl-2,3-O-isopropylidene-4-O-p-methoxybenzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: With magnesium; mercury dibromide; In tetrahydrofuran; at 10 - 20 ℃;
DOI:10.1016/S0957-4166(99)00554-6

Reference yield:

: 7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3
ethyl 1-thio-α-D-mannopyranoside

: 286845-66-7
ethyl 7-O-benzyl-2,3-O-isopropylidene-4-O-p-methoxybenzyl-1-thio-D-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: pyridine; 4-dimethylaminopyridine

2.1: p-toluenesulfonic acid / dimethylformamide / 2 h / 20 °C

3.1: NaH / dimethylformamide / 1 h / 0 °C

3.2: 80 percent / dimethylformamide / 2 h / 0 °C

4.1: 62 percent / aq. formic acid / ethyl acetate / 2.5 h

5.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.5 h / -60 °C

6.1: 21 percent / Mg; HgBr₂ / tetrahydrofuran / 10 - 20 °C

With pyridine; dmap; formic acid; oxalyl dichloride; sodium hydride; toluene-4-sulfonic acid; magnesium; dimethyl sulfoxide; mercury dibromide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Alkylation / 2.1: acetalization / 3.1: Metallation / 3.2: Substitution / 4.1: Hydrolysis / 5.1: Oxidation / 6.1: Grignard reaction;
DOI:10.1016/S0957-4166(99)00554-6

Reference yield:

: 128850-48-6
ethyl 1-thio-6-O-triphenylmethyl-α-D-mannopyranoside

: 286845-66-7
ethyl 7-O-benzyl-2,3-O-isopropylidene-4-O-p-methoxybenzyl-1-thio-D-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: p-toluenesulfonic acid / dimethylformamide / 2 h / 20 °C

2.1: NaH / dimethylformamide / 1 h / 0 °C

2.2: 80 percent / dimethylformamide / 2 h / 0 °C

3.1: 62 percent / aq. formic acid / ethyl acetate / 2.5 h

4.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.5 h / -60 °C

5.1: 21 percent / Mg; HgBr₂ / tetrahydrofuran / 10 - 20 °C

With formic acid; oxalyl dichloride; sodium hydride; toluene-4-sulfonic acid; magnesium; dimethyl sulfoxide; mercury dibromide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: acetalization / 2.1: Metallation / 2.2: Substitution / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: Grignard reaction;
DOI:10.1016/S0957-4166(99)00554-6