phenyl 2,6-di-O-benzoyl-3,4-O-(isopropylidene)-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 2,6-di-O-benzoyl-3,4-O-(isopropylidene)-1-thio-β-D-galactopyranoside
• CAS No.: 124477-00-5
• Molecular Formula: C₂₉H₂₈O₇S
• Molecular Weight: 520.603

Synonyms:phenyl 2,6-di-O-benzoyl-3,4-O-(isopropylidene)-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 2,6-di-O-benzoyl-3,4-O-(isopropylidene)-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of phenyl 2,6-di-O-benzoyl-3,4-O-(isopropylidene)-1-thio-β-D-galactopyranoside

There total 6 articles about phenyl 2,6-di-O-benzoyl-3,4-O-(isopropylidene)-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:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → phenyl 2,6-di-O-benzoyl-3,4-O-(isopropylidene)-1-thio-β-D-galactopyranoside (124477-00-5)

Guidance literature:

Multi-step reaction with 2 steps

1: CSA

2: pyridine / CH₂Cl₂

With pyridine; camphor-10-sulfonic acid; In dichloromethane;

DOI:10.1016/j.tetasy.2004.12.004

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 2,6-di-O-benzoyl-3,4-O-(isopropylidene)-1-thio-β-D-galactopyranoside (124477-00-5)

Guidance literature:

Multi-step reaction with 3 steps

1: (+/-)-10 CSA / 48 h / Ambient temperature

2: acidic work-up

3: 86 percent / 4-DMAP / pyridine / 0.08 h / 0 °C

With dmap; 10-camphorsufonic acid; In pyridine;

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

Reference yield:

phenyl 2,6-di-O-acetyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (124476-99-9) → phenyl 2,6-di-O-benzoyl-3,4-O-(isopropylidene)-1-thio-β-D-galactopyranoside (124477-00-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 17 percent / lithium naphthalenide / tetrahydrofuran / 0.25 h / -78 - 25 °C

2: 86 percent / 4-DMAP / pyridine / 0.08 h / 0 °C

With dmap; naphthalen-1-yl-lithium; In tetrahydrofuran; pyridine;

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

upstream raw materials:

1-thiophenyl-β-D-galactopyranoside

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

phenyl 2,6-di-O-acetyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

phenyl 1-thio-3,4-O-isopropylidene-6-O-(1-methoxyl-1-methylethyl)-β-D-galactopyranoside

Downstream raw materials:

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

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

phenyl 2,6-di-O-benzoyl-1-thio-β-thio-β-D-galactopyranoside

methyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->6)-[2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->3)]-2-O-acetyl-α-D-galactopyranoside

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