Methyl O-{2,4,6-tri-O-acetyl-3-O-[(S)-1-(methoxycarbonyl)ethyl]-β-D-galactopyranosyl}-(1->4)-O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

Base Information

Chemical Name:Methyl O-{2,4,6-tri-O-acetyl-3-O-[(S)-1-(methoxycarbonyl)ethyl]-β-D-galactopyranosyl}-(1->4)-O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside
CAS No.:177421-17-9
Molecular Formula:C₆₇H₇₄ClNO₂₃
Molecular Weight:1296.77
Hs Code.:

Methyl O-{2,4,6-tri-O-acetyl-3-O-[(S)-1-(methoxycarbonyl)ethyl]-β-D-galactopyranosyl}-(1->4)-O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

Synonyms:Methyl O-{2,4,6-tri-O-acetyl-3-O-[(S)-1-(methoxycarbonyl)ethyl]-β-D-galactopyranosyl}-(1->4)-O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

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Chemical Property of Methyl O-{2,4,6-tri-O-acetyl-3-O-[(S)-1-(methoxycarbonyl)ethyl]-β-D-galactopyranosyl}-(1->4)-O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

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Technology Process of Methyl O-{2,4,6-tri-O-acetyl-3-O-[(S)-1-(methoxycarbonyl)ethyl]-β-D-galactopyranosyl}-(1->4)-O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

There total 13 articles about Methyl O-{2,4,6-tri-O-acetyl-3-O-[(S)-1-(methoxycarbonyl)ethyl]-β-D-galactopyranosyl}-(1->4)-O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-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: 63.0%

: 177421-11-3
(S)-2-[(2R,3S,4S,5R,6R)-3,5-Diacetoxy-2-acetoxymethyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yloxy]-propionic acid methyl ester

: 177421-16-8
Chloro-acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-6-((2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

: 177421-17-9
Methyl O-{2,4,6-tri-O-acetyl-3-O-[(S)-1-(methoxycarbonyl)ethyl]-β-D-galactopyranosyl}-(1->4)-O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; 1.) r.t., 1 h, 2.) -45 deg C, 2 h;
DOI:10.1080/07328309608005652

Reference yield:

: 55697-53-5
methyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside

: 177421-17-9
Methyl O-{2,4,6-tri-O-acetyl-3-O-[(S)-1-(methoxycarbonyl)ethyl]-β-D-galactopyranosyl}-(1->4)-O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 57.2 percent / NaH / dimethylformamide / 1.) 60 deg C, 1 h, 2.) 60 deg C, 24 h

2: 97 percent / H₂ / 10percent Pd/C / methanol; H₂O / 3 h / 1810.02 - 2068.6 Torr

3: 99 percent / pyridine

4: 94.6 percent / 1,1-dichloromethyl methyl ether, ZnCl₂ / CH₂Cl₂ / 2 h / Ambient temperature

5: 85.2 percent / silver triflate, 2,6-lutidine / 2 h / Ambient temperature

6: hydrazine acetate / dimethylformamide / 2 h / 60 °C

7: 58.9 percent / DBU / CH₂Cl₂ / 2 h / 0 °C

8: 63 percent / trimethylsilyl triflate, molecular sieves 4 Angstroem / CH₂Cl₂ / 1.) r.t., 1 h, 2.) -45 deg C, 2 h

With pyridine; 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; Dichloromethyl methyl ether; 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; hydrazinium monoacetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride; palladium on activated charcoal; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1080/07328309608005652

Reference yield:

: 93253-14-6
methyl 3-O-allyl-2,4,6-tri-O-benzyl-β-D-galactopyranoside

: 177421-17-9
Methyl O-{2,4,6-tri-O-acetyl-3-O-[(S)-1-(methoxycarbonyl)ethyl]-β-D-galactopyranosyl}-(1->4)-O-(3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: 88 percent / PdCl₂ / methanol / Ambient temperature

2: 57.2 percent / NaH / dimethylformamide / 1.) 60 deg C, 1 h, 2.) 60 deg C, 24 h

3: 97 percent / H₂ / 10percent Pd/C / methanol; H₂O / 3 h / 1810.02 - 2068.6 Torr

4: 99 percent / pyridine

5: 94.6 percent / 1,1-dichloromethyl methyl ether, ZnCl₂ / CH₂Cl₂ / 2 h / Ambient temperature

6: 85.2 percent / silver triflate, 2,6-lutidine / 2 h / Ambient temperature

7: hydrazine acetate / dimethylformamide / 2 h / 60 °C

8: 58.9 percent / DBU / CH₂Cl₂ / 2 h / 0 °C

9: 63 percent / trimethylsilyl triflate, molecular sieves 4 Angstroem / CH₂Cl₂ / 1.) r.t., 1 h, 2.) -45 deg C, 2 h

With pyridine; 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; Dichloromethyl methyl ether; 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; hydrazinium monoacetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; zinc(II) chloride; palladium on activated charcoal; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1080/07328309608005652