methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 3)-4-O-benzoyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 3)-4-O-benzoyl-α-L-rhamnopyranoside
• CAS No.: 388566-67-4
• Molecular Formula: C₃₇H₃₇NO₁₃
• Molecular Weight: 703.7
• Mol file: 388566-67-4.mol

Synonyms:methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 3)-4-O-benzoyl-α-L-rhamnopyranoside

Chemical Property of methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 3)-4-O-benzoyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 3)-4-O-benzoyl-α-L-rhamnopyranoside

There total 1 articles about methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 3)-4-O-benzoyl-α-L-rhamnopyranoside 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: 59.0%

methyl 4-O-benzyl-α-L-rhamnopyranoside (25019-69-6) + ethyl 3-O-acetyl-4,6-O-benzylidene-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (125520-04-9) → Benzoic acid (2S,3R,4R,5R,6R)-5-[(2R,4aR,6S,7R,8R,8aS)-8-acetoxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-4-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester + methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 3)-4-O-benzoyl-α-L-rhamnopyranoside (388566-67-4) + Benzoic acid (2S,3S,4R,5R,6R)-4,5-bis-[(2R,4aR,6S,7R,8R,8aS)-8-acetoxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:

With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -30 - -10 ℃; for 0.5h;

DOI:10.1002/1099-0690(200109)2001:18<3453::AID-EJOC3453>3.0.CO;2-#

Reference yield: 90.0%

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl trichloroacetimidate (83025-11-0) + methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 3)-4-O-benzoyl-α-L-rhamnopyranoside (388566-67-4) → methyl 3,4,6-tri-O-acetyl-2-deoxy-2-azido-α-D-galactopyranosyl-(1-> 2)-[3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 3)]-4-O-benzoyl-α-L-rhamnopyranoside (388566-68-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In diethyl ether; at -20 ℃; for 0.333333h;

DOI:10.1002/1099-0690(200109)2001:18<3453::AID-EJOC3453>3.0.CO;2-#

Reference yield:

methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 3)-4-O-benzoyl-α-L-rhamnopyranoside (388566-67-4) → methyl 2-deoxy-2-N-acetyl-α-D-galactopyranosyl-(1-> 2)-[4,6-O-benzylidene-2-deoxy-2-N-acetyl-β-D glucopyranosyl-(1-> 3)]-α-L-rhamnopyranoside (388566-71-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / TMSOTf; molecular sieves 4 Angstroem / diethyl ether / 0.33 h / -20 °C

2: ethylenediamine / butan-1-ol / 4 h / 90 °C

3: pyridine / 1 h / 20 °C

4: 90 percent / pyridine / 36 h / 20 °C

5: 89 percent / NaOMe / methanol / 1.5 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; ethylenediamine; In pyridine; methanol; diethyl ether; butan-1-ol;

DOI:10.1002/1099-0690(200109)2001:18<3453::AID-EJOC3453>3.0.CO;2-#

upstream raw materials:

methyl 4-O-benzyl-α-L-rhamnopyranoside

ethyl 3-O-acetyl-4,6-O-benzylidene-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

methyl 3,4,6-tri-O-acetyl-2-deoxy-2-azido-α-D-galactopyranosyl-(1-> 2)-[3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1-> 3)]-4-O-benzoyl-α-L-rhamnopyranoside

methyl 2-deoxy-2-N-acetyl-α-D-galactopyranosyl-(1-> 2)-[4,6-O-benzylidene-2-deoxy-2-N-acetyl-β-D glucopyranosyl-(1-> 3)]-α-L-rhamnopyranoside

benzoic acid 4-(8-acetoxy-7-acetylamino-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5-(4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

benzoic acid 4-(8-acetoxy-7-acetylamino-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester