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

Base Information

Chemical Name:4-methoxyphenyl 4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
CAS No.:583041-04-7
Molecular Formula:C₅₀H₄₄ClNO₁₅
Molecular Weight:934.35
Hs Code.:

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

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

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

There total 10 articles about 4-methoxyphenyl 4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-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: 54.9%

: 583041-02-5
4-methoxyphenyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside

: 583040-98-6
ethyl 4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 583041-04-7
4-methoxyphenyl 4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; for 0.75h;
DOI:10.1081/CAR-120020480

Reference yield:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 583041-04-7
4-methoxyphenyl 4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 62.5 percent / BF₃*Et₂O / CH₂Cl₂ / 22 h

2: 69.5 percent / sodium methoxide / methanol / 3 h

3: 77.5 percent / p-toluenesulfonic acid; molecular sieves 3 Angstroem / acetonitrile

4: 83 percent / triethylamine / CH₂Cl₂ / 3 h

5: 54.9 percent / N-iodosuccinimide; trifluoromethanesulfonic acid; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.75 h

With N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; acetonitrile;
DOI:10.1081/CAR-120020480

Reference yield:

: 18918-36-0
4-methoxyphenyl α-L-rhamnopyranoside

: 583041-04-7
4-methoxyphenyl 4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 73 percent / p-toluenesulfonic acid / dimethylformamide / 5 h / 20 °C

2.1: 92 percent / pyridine / 4 h / 20 °C

3.1: 83.5 percent / acetic acid / H₂O / 2 h / 80 °C

4.1: (+/-) camphor-10-sulfonic acid / CH₂Cl₂ / 0.25 h

4.2: 2.68 g / acetic acid / H₂O / 0.5 h / 20 °C

5.1: 54.9 percent / N-iodosuccinimide; trifluoromethanesulfonic acid; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.75 h

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; 10-camphorsufonic acid; toluene-4-sulfonic acid; acetic acid; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1081/CAR-120020480