p-methylphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranose

Base Information

• Chemical Name: p-methylphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranose
• CAS No.: 634197-71-0
• Molecular Formula: C₃₆H₃₈O₆S
• Molecular Weight: 598.76

Synonyms:p-methylphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranose

Chemical Property of p-methylphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranose

Chemical Property:

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Technology Process of p-methylphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranose

There total 6 articles about p-methylphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranose 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: 80.0%

3,4,6-tri-O-benzyl-1,2-O-[1-(ethylsulfanyl)ethylidene]-α-D-glucopyranose (852448-25-0) + para-thiocresol (106-45-6) → p-methylphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranose (634197-71-0)

Guidance literature:

3,4,6-tri-O-benzyl-1,2-O-[1-(ethylsulfanyl)ethylidene]-α-D-glucopyranose; para-thiocresol; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; for 12h; Molecular sieve; Inert atmosphere;

DOI:10.1039/c9cc07194f

Reference yield: 67.0%

para-thiocresol (106-45-6) + 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose (158852-31-4) → p-methylphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranose (634197-71-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1021/ol048427o

Reference yield: 58.0%

3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose (51532-75-3,16697-49-7,68681-00-5,68779-52-2,78418-56-1,125135-29-7,130694-47-2,130694-49-4,146864-77-9) + para-thiocresol (106-45-6) → p-methylphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranose (634197-71-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -15 - 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201100732

upstream raw materials:

para-thiocresol

3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose

D-glucose pentaacetate

3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose

Downstream raw materials:

(3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-ethyl-3aH,5H,6H,7H,7aH-pyrano[2,3-d][1,3]oxazole

6-chlorohexyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside

4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranos-4-O-yl)ethyl)-1-thio-β-D-glucopyranoside

p-methylphenyl 3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside

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