phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside
• CAS No.: 179072-54-9
• Molecular Formula: C₂₆H₂₅NO₉S
• Molecular Weight: 527.552

Synonyms:phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

Chemical Property:

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Technology Process of phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

There total 4 articles about phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-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: 36.0%

→ phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (179072-54-9)

Guidance literature:

Reference yield:

thiophenol (108-98-5) + p-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranoside (163121-75-3) → phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (179072-54-9) + phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-α-D-galactopyranoside

Guidance literature:

With boron trifluoride diethyl etherate; In chloroform; at 60 ℃; Yield given. Yields of byproduct given;

DOI:10.1016/S0008-6215(96)90118-4

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranoside (81704-02-1) → phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (179072-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / BF₃*Et₂O / CH₂Cl₂

2: BF₃*Et₂O / CHCl₃ / 60 °C

With boron trifluoride diethyl etherate; In dichloromethane; chloroform;

DOI:10.1016/S0008-6215(96)90118-4

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-α,β-D-galactopyranose

thiophenol

p-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

Downstream raw materials:

Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3S,4S,5R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(2R,3S,4R,5R,6R)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

phenyl 2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside

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