phenyl 2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside
• CAS No.: 273749-71-6
• Molecular Formula: C₃₀H₃₈O₈S
• Molecular Weight: 558.693

Synonyms:phenyl 2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside

Chemical Property:

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Technology Process of phenyl 2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside

There total 5 articles about phenyl 2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside 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: 92.0%

pivaloyl chloride (3282-30-2) + phenyl 4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside (273749-60-3) → phenyl 2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside (273749-71-6)

Guidance literature:

With dmap; In pyridine; for 12h; Heating;

DOI:10.1021/ol0057075

Reference yield:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (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) → phenyl 2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside (273749-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / p-TsOH*H₂O / dimethylformamide / 2 h / 50 °C

2: 92 percent / DMAP / pyridine / 12 h / Heating

With dmap; toluene-4-sulfonic acid; In pyridine; N,N-dimethyl-formamide; 1: Etherification / 2: Acylation;

DOI:10.1021/ol0057075

Reference yield:

thiophenol (108-98-5) → phenyl 2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside (273749-71-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / tetrabutylammonium hydrogen sulfate; Na₂CO₃ / CH₂Cl₂ / 0.75 h / 25 °C

2: 99 percent / Na / methanol / 3 h / 20 °C

3: 88 percent / p-TsOH*H₂O / dimethylformamide / 2 h / 50 °C

4: 92 percent / DMAP / pyridine / 12 h / Heating

With dmap; tetra(n-butyl)ammonium hydrogensulfate; sodium; sodium carbonate; toluene-4-sulfonic acid; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Deacetylation / 3: Etherification / 4: Acylation;

DOI:10.1021/ol0057075

upstream raw materials:

pivaloyl chloride

phenyl 4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

thiophenol

Downstream raw materials:

methyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

methyl O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranoside)

6-(7-acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid

methyl O-(2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl)-(1->3)-(2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside)

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