p-octyloxyphenyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: p-octyloxyphenyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
• CAS No.: 916497-81-9
• Molecular Formula: C₃₄H₄₁NO₁₀S
• Molecular Weight: 655.766

Synonyms:p-octyloxyphenyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside

Chemical Property of p-octyloxyphenyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of p-octyloxyphenyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside

There total 4 articles about p-octyloxyphenyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-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: 89.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) + p-octyloxybenzenethiol (102231-96-9) → p-octyloxyphenyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside (916497-81-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 20h;

DOI:10.1248/cpb.c16-00203

Reference yield: 89.0%

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (72858-55-0,90405-21-3,90405-42-8,124362-60-3,144221-86-3) + p-octyloxybenzenethiol (102231-96-9) → p-octyloxyphenyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside (916497-81-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 20h;

DOI:10.1002/ejoc.201500186

Reference yield:

4-(octyloxy)benzene-1-sulfonyl chloride (21095-40-9) → p-octyloxyphenyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside (916497-81-9)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminum hydride / tetrahydrofuran / 10 h / Heating

2: 89 percent / boron trifluoride diethyl etherate / CH₂Cl₂ / 12 h / 20 °C

With lithium aluminium tetrahydride; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2006.08.095

upstream raw materials:

4-(octyloxy)benzene-1-sulfonyl chloride

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

p-octyloxybenzenethiol

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

Downstream raw materials:

3,4,6-tri-O-acetyl-2-N-phthaloyl-β(1-6)-D-glucosaminyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyl p-octyloxyphenyl sulfoxide

3,4,6-tri-O-acetyl-2-N-phthaloyl-β(1-2)-D-glucosaminyl-3-O-benzyl-(4,6)-benzylidene-β-D-mannopyranosyl p-octyloxyphenyl sulfoxide

C₇₂H₈₁NO₂₀Si

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