methyl β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: methyl β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 129090-85-3
• Molecular Formula: C₃₅H₃₉NO₁₂
• Molecular Weight: 665.694
• Mol file: 129090-85-3.mol

Synonyms:

Chemical Property of methyl β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 20 articles about methyl β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-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:

methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (97242-79-0) → methyl β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (129090-85-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / molecular sieves 4A; trimethylsilyl triflate / CH₂Cl₂ / 5 h / -30 - -20 °C

2: MeONa; MeOH / 0.25 h / 20 °C

With methanol; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; In dichloromethane;

DOI:10.1560/LXUM-GKYP-R6RF-08TF

Reference yield:

methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (100638-50-4,151434-35-4,129172-96-9) → methyl β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (129090-85-3)

Guidance literature:

With methanol; sodium methylate; for 2h; Ambient temperature;

DOI:10.1016/0008-6215(90)84225-J

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → methyl β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (129090-85-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: boron trifluoride diethyl etherate / chloroform / 0.17 h / 0 - 20 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: methanol; sodium methylate / 1.5 h / 20 °C / pH 9

3.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 - 50 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: hydrogenchloride; sodium cyanoborohydride / tetrahydrofuran; diethyl ether / 5 h / 0 - 20 °C / Molecular sieve

6.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.17 h / 20 °C / Inert atmosphere

7.1: silver trifluoromethanesulfonate / dichloromethane; toluene / 4.5 h / -40 °C / Molecular sieve; Inert atmosphere

8.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 1 h / 20 °C / Inert atmosphere

9.1: methanol; sodium methylate / 0.5 h / pH 9

With hydrogenchloride; methanol; N-iodo-succinimide; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1039/c2ob07066a

upstream raw materials:

methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

β-D-galactose peracetate

methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

2-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

2-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-6-allyloxymethyl-3,5-dihydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Benzoic acid (4aR,6S,7R,8R,8aS)-6-[(2R,3S,4R,5R,6R)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methoxy-tetrahydro-pyran-3-yloxy]-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

C₇₃H₆₉NO₂₂

Refernces

• 1、 Duus, Jens .,Nifant'ev, Nikolay E.,Shashkov, Alexander S.,Khatuntseva, Elena A.,Bock, Klaus. "Synthesis and structural studies of "branched" 2-linked trisaccharides related to H-type 2 blood group determinants". . p. 223 - 239. Retrieved 2007/10/03.