p-tolyl 2,3-anhydro-5,6-di-O-benzyl-1-thio-β-D-gulofuranoside

Base Information

Chemical Name:p-tolyl 2,3-anhydro-5,6-di-O-benzyl-1-thio-β-D-gulofuranoside
CAS No.:920267-51-2
Molecular Formula:C₂₇H₂₈O₄S
Molecular Weight:448.583
Hs Code.:

Synonyms:p-tolyl 2,3-anhydro-5,6-di-O-benzyl-1-thio-β-D-gulofuranoside

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Chemical Property of p-tolyl 2,3-anhydro-5,6-di-O-benzyl-1-thio-β-D-gulofuranoside

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Technology Process of p-tolyl 2,3-anhydro-5,6-di-O-benzyl-1-thio-β-D-gulofuranoside

There total 7 articles about p-tolyl 2,3-anhydro-5,6-di-O-benzyl-1-thio-β-D-gulofuranoside 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%

: 920267-59-0
p-tolyl 2,3-anhydro-1-thio-β-D-gulofuranoside

: 100-39-0
benzyl bromide

: 920267-51-2
p-tolyl 2,3-anhydro-5,6-di-O-benzyl-1-thio-β-D-gulofuranoside

Guidance literature:: p-tolyl 2,3-anhydro-1-thio-β-D-gulofuranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.0833333h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 6h;
DOI:10.1021/jo061713o

Reference yield:

: (1R,2S,4S,5R)-2-((R)-2-Methoxy-2-methyl-[1,3]dioxolan-4-yl)-4-p-tolylsulfanyl-3,6-dioxa-bicyclo[3.1.0]hexane

: 920267-51-2
p-tolyl 2,3-anhydro-5,6-di-O-benzyl-1-thio-β-D-gulofuranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: aq. HCl / ethyl acetate / 20 °C

1.2: 1.32 g / NaOCH₃ / methanol; CH₂Cl₂ / 14 h / 20 °C / pH 10

2.1: NaH / dimethylformamide; various solvent(s) / 0.08 h / 0 °C

2.2: 93 percent / dimethylformamide; various solvent(s) / 6 h / 20 °C

With hydrogenchloride; sodium hydride; In ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo061713o

Reference yield:

: 920267-56-7
4-methylphenyl 1-thio-β-D-galactofuranoside

: 920267-51-2
p-tolyl 2,3-anhydro-5,6-di-O-benzyl-1-thio-β-D-gulofuranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: p-toluenesulfonic acid / tetrahydrofuran / 3 h / 20 °C

2.1: PPh₃; diisopropylazodicarboxylate / 1 h / 0 - 20 °C

3.1: aq. HCl / ethyl acetate / 20 °C

3.2: 1.32 g / NaOCH₃ / methanol; CH₂Cl₂ / 14 h / 20 °C / pH 10

4.1: NaH / dimethylformamide; various solvent(s) / 0.08 h / 0 °C

4.2: 93 percent / dimethylformamide; various solvent(s) / 6 h / 20 °C

With hydrogenchloride; di-isopropyl azodicarboxylate; sodium hydride; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo061713o