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

Base Information

• Chemical Name: p-Methoxyphenyl O-(2,4-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 138906-46-4
• Molecular Formula: C₅₅H₅₅NO₁₃
• Molecular Weight: 938.041
• Mol file: 138906-46-4.mol

Synonyms:p-Methoxyphenyl O-(2,4-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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

There total 11 articles about p-Methoxyphenyl O-(2,4-di-O-benzyl-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:

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-{(2S,3R,4S,5S,6R)-3,5-bis-benzyloxy-4-[((E)-propenyl)oxy]-6-[((E)-propenyl)oxymethyl]-tetrahydro-pyran-2-yloxy}-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione → p-Methoxyphenyl O-(2,4-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (138906-46-4)

Guidance literature:

With mercury dichloride; mercury(II) oxide; In water; acetone; at 20 ℃; for 2h; Yield given;

DOI:10.1016/0008-6215(93)84080-P

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → p-Methoxyphenyl O-(2,4-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (138906-46-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 84 percent / Me₃SiOTf / 1,2-dichloro-ethane / 3 h / 0 °C

2: p-TsOH*H₂O / dimethylformamide / 20 h / 20 °C

3: 61 percent / NaH / dimethylformamide / 20 h / 20 °C

4: 77 percent / p-TsOH*H₂O / methanol; dioxane / 1) 1 h, 60 deg C, 2) 45 min, 85 deg C

6: 91 percent / AgOTf, 4A moleculat sieves / 1,2-dichloro-ethane / -20 °C

7: 67 percent / 1.25N LiOH, 31percent H₂O₂ / tetrahydrofuran / 8 h / 0 °C

8: 98 percent / Ag₂O, KI / dimethylformamide / 1) 1 h, 0 deg C, 2) 1 h, 20 deg C

9: (Ph₃P)RhCl, DABCO / ethanol; acetonitrile; H₂O / 72 h / Heating

10: HgCl₂, HgO / acetone; H₂O / 2 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; (Ph₃P)RhCl; 4 A molecular sieve; dihydrogen peroxide; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; potassium iodide; mercury dichloride; mercury(II) oxide; silver(l) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/0008-6215(93)84080-P

Reference yield:

p-Methoxyphenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (129575-88-8) → p-Methoxyphenyl O-(2,4-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (138906-46-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 77 percent / p-TsOH*H₂O / methanol; dioxane / 1) 1 h, 60 deg C, 2) 45 min, 85 deg C

3: 91 percent / AgOTf, 4A moleculat sieves / 1,2-dichloro-ethane / -20 °C

4: 67 percent / 1.25N LiOH, 31percent H₂O₂ / tetrahydrofuran / 8 h / 0 °C

5: 98 percent / Ag₂O, KI / dimethylformamide / 1) 1 h, 0 deg C, 2) 1 h, 20 deg C

6: (Ph₃P)RhCl, DABCO / ethanol; acetonitrile; H₂O / 72 h / Heating

7: HgCl₂, HgO / acetone; H₂O / 2 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; lithium hydroxide; (Ph₃P)RhCl; 4 A molecular sieve; dihydrogen peroxide; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; potassium iodide; mercury dichloride; mercury(II) oxide; silver(l) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/0008-6215(93)84080-P

upstream raw materials:

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

4-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside

p-Methoxyphenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

O-(2,4-di-O-Benzyl-3-O-levulinoyl-6-O-pivaloyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose

4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl ester

4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-fluoro-tetrahydro-pyran-3-yloxy]-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl ester

4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6R)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxy-tetrahydro-pyran-3-yloxy]-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl ester