12-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxy]-dodecanoic acid methyl ester

Base Information

• Chemical Name: 12-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxy]-dodecanoic acid methyl ester
• CAS No.: 200998-93-2
• Molecular Formula: C₄₉H₆₆O₈Si
• Molecular Weight: 811.144

Synonyms:12-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxy]-dodecanoic acid methyl ester

Chemical Property of 12-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxy]-dodecanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 12-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxy]-dodecanoic acid methyl ester

There total 4 articles about 12-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxy]-dodecanoic acid methyl 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: 78.0%

methyl 12-hydroxydodecanoate (71655-36-2) + ((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) → 12-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxy]-dodecanoic acid methyl ester (200998-93-2)

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:

1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enitol (87316-22-1,137893-35-7) → 12-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxy]-dodecanoic acid methyl ester (200998-93-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / 1.) NaH; 2.) methyltriphenylphosphonium iodide / tetrahydrofuran; paraffin / 3 h / 30 °C / 1.) 10 min

2: 3,3-dimethyloxirane / CH₂Cl₂; acetone / 0.02 h / 0 °C

3: 78 percent / ZnCl₂ / tetrahydrofuran / 0.17 h / 0 °C

With 2-methyl-1,2-epoxypropane; methyl-triphenylphosphonium iodide; sodium hydride; zinc(II) chloride; In tetrahydrofuran; dichloromethane; acetone; paraffin;

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

Reference yield:

benzyl bromide (100-39-0) → 12-[(2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-tetrahydro-pyran-2-yloxy]-dodecanoic acid methyl ester (200998-93-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / 1.) NaH; 2.) methyltriphenylphosphonium iodide / tetrahydrofuran; paraffin / 3 h / 30 °C / 1.) 10 min

2: 3,3-dimethyloxirane / CH₂Cl₂; acetone / 0.02 h / 0 °C

3: 78 percent / ZnCl₂ / tetrahydrofuran / 0.17 h / 0 °C

With 2-methyl-1,2-epoxypropane; methyl-triphenylphosphonium iodide; sodium hydride; zinc(II) chloride; In tetrahydrofuran; dichloromethane; acetone; paraffin;

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

upstream raw materials:

methyl 12-hydroxydodecanoate

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

1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enitol

benzyl bromide

Downstream raw materials:

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

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

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-3,4-di-O-benzyl-β-D-galactopyranoside

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