Benzoic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxymethyl]-2-(11-methoxycarbonyl-undecyloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxymethyl]-2-(11-methoxycarbonyl-undecyloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 200998-98-7
• Molecular Formula: C₇₆H₉₂O₁₄Si
• Molecular Weight: 1257.64

Synonyms:Benzoic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxymethyl]-2-(11-methoxycarbonyl-undecyloxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxymethyl]-2-(11-methoxycarbonyl-undecyloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Benzoic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxymethyl]-2-(11-methoxycarbonyl-undecyloxy)-tetrahydro-pyran-3-yl ester

There total 6 articles about Benzoic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxymethyl]-2-(11-methoxycarbonyl-undecyloxy)-tetrahydro-pyran-3-yl ester 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: 71.0%

((1S,3R,4S,5S,6R)-4,5-Bis-benzyloxy-2,7-dioxa-bicyclo[4.1.0]hept-3-ylmethoxy)-tert-butyl-diphenyl-silane (195724-13-1) + 11-methoxycarbonylundecanyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-galactopyranoside (200998-95-4) → Benzoic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxymethyl]-2-(11-methoxycarbonyl-undecyloxy)-tetrahydro-pyran-3-yl ester (200998-98-7)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

DOI:10.1002/(sici)1099-0690(199801)1998:1<91::aid-ejoc91>3.0.co;2-n

Reference yield:

3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-D-galactal (201800-34-2) → Benzoic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxymethyl]-2-(11-methoxycarbonyl-undecyloxy)-tetrahydro-pyran-3-yl ester (200998-98-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 3,3-dimethyloxirane / CH₂Cl₂; acetone / 0.02 h / 0 °C

2: 78 percent / ZnCl₂ / tetrahydrofuran / 0.17 h / 0 °C

3: 91 percent / pyridine / 3 h

4: 82 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h

5: 71 percent / ZnCl₂ / tetrahydrofuran / 0.17 h / 0 °C

With 2-methyl-1,2-epoxypropane; pyridine; tetrabutyl ammonium fluoride; zinc(II) chloride; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1002/(sici)1099-0690(199801)1998:1<91::aid-ejoc91>3.0.co;2-n

Reference yield:

methyl 12-hydroxydodecanoate (71655-36-2) → Benzoic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxymethyl]-2-(11-methoxycarbonyl-undecyloxy)-tetrahydro-pyran-3-yl ester (200998-98-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / ZnCl₂ / tetrahydrofuran / 0.17 h / 0 °C

2: 91 percent / pyridine / 3 h

3: 82 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h

4: 71 percent / ZnCl₂ / tetrahydrofuran / 0.17 h / 0 °C

With pyridine; tetrabutyl ammonium fluoride; zinc(II) chloride; In tetrahydrofuran;

DOI:10.1002/(sici)1099-0690(199801)1998:1<91::aid-ejoc91>3.0.co;2-n

upstream raw materials:

((1S,3R,4S,5S,6R)-4,5-Bis-benzyloxy-2,7-dioxa-bicyclo[4.1.0]hept-3-ylmethoxy)-tert-butyl-diphenyl-silane

11-methoxycarbonylundecanyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-galactopyranoside

methyl 12-hydroxydodecanoate

3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-D-galactal

Downstream raw materials:

11-methoxycarbonylundecanyl 2-O-benzoyl-6-O-(2-O-benzoyl-3,4-di-O-benzyl-β-D-galactopyranosyl)-3,4-di-O-benzyl-β-D-galactopyranoside

11-methoxycarbonylundecanyl 2-O-benzoyl-6-O-(2-O-benzoyl-3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-galactopyranosyl)-3,4-di-O-benzyl-β-D-galactopyranoside

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