Phenyl 3,4-O-(1-methylethylidene)-1-thio-beta-D-galactopyranoside diacetate

Base Information

• Chemical Name: Phenyl 3,4-O-(1-methylethylidene)-1-thio-beta-D-galactopyranoside diacetate
• CAS No.: 124476-99-9
• Molecular Formula: C19H24O7S
• Molecular Weight: 396.45
• Mol file: 124476-99-9.mol

Synonyms:Phenyl 3,4-O-(1-methylethylidene)-1-thio-beta-D-galactopyranoside diacetate

Chemical Property of Phenyl 3,4-O-(1-methylethylidene)-1-thio-beta-D-galactopyranoside diacetate

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Phenyl 2,6-di-O-acetyl-3,4-O-isopropylidene-b-D-thiogalactopyranoside ^*data from reagent suppliers

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Technology Process of Phenyl 3,4-O-(1-methylethylidene)-1-thio-beta-D-galactopyranoside diacetate

There total 9 articles about Phenyl 3,4-O-(1-methylethylidene)-1-thio-beta-D-galactopyranoside diacetate 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: 95.0%

acetic anhydride (108-24-7) + phenyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (120095-47-8) → phenyl 2,6-di-O-acetyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (124476-99-9)

Guidance literature:

In pyridine; for 3h; Ambient temperature;

DOI:10.1016/0008-6215(89)84061-3

Reference yield: 88.0%

phenyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (120095-47-8) + acetyl chloride (75-36-5) → phenyl 2,6-di-O-acetyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (124476-99-9) + phenyl 6-O-acetyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (171815-42-2)

Guidance literature:

With 2,4,6-trimethyl-pyridine; In dichloromethane; at -78 ℃; for 2h; Yield given;

DOI:10.1021/jo00126a065

Reference yield:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → phenyl 2,6-di-O-acetyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (124476-99-9)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂SO₄ / dimethylformamide; acetone / 20 h / Ambient temperature

2: sym-collidine / CH₂Cl₂ / 2 h / -78 °C

With 2,4,6-trimethyl-pyridine; sulfuric acid; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00126a065

upstream raw materials:

acetic anhydride

phenyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

acetyl chloride

1-thiophenyl-β-D-galactopyranoside

Downstream raw materials:

2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl phenyl sulphone

2,6-anhydro-5-deoxy-3,4-O-isopropylidene-D-arabino-hex-5-enitol

phenyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

1,5-anhydro-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-D-lyxo-hex-1-enitol

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