Benzoic acid (2S,3R,4R,5R,6R)-5-hydroxy-6-hydroxymethyl-4-methanesulfonyloxy-5-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4R,5R,6R)-5-hydroxy-6-hydroxymethyl-4-methanesulfonyloxy-5-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester
• CAS No.: 359766-28-2
• Molecular Formula: C₂₄H₄₀O₉SSi
• Molecular Weight: 532.728
• Mol file: 359766-28-2.mol

Synonyms:Benzoic acid (2S,3R,4R,5R,6R)-5-hydroxy-6-hydroxymethyl-4-methanesulfonyloxy-5-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3R,4R,5R,6R)-5-hydroxy-6-hydroxymethyl-4-methanesulfonyloxy-5-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,3R,4R,5R,6R)-5-hydroxy-6-hydroxymethyl-4-methanesulfonyloxy-5-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

There total 12 articles about Benzoic acid (2S,3R,4R,5R,6R)-5-hydroxy-6-hydroxymethyl-4-methanesulfonyloxy-5-methyl-2-triisopropylsilanyloxy-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: 95.0%

Benzoic acid (2S,3R,4R,5R,6R)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4-methanesulfonyloxy-5-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester (359766-27-1) → Benzoic acid (2S,3R,4R,5R,6R)-5-hydroxy-6-hydroxymethyl-4-methanesulfonyloxy-5-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester (359766-28-2)

Guidance literature:

With boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; In tetrahydrofuran; acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/ol010089t

Reference yield:

benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside (79549-73-8) → Benzoic acid (2S,3R,4R,5R,6R)-5-hydroxy-6-hydroxymethyl-4-methanesulfonyloxy-5-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester (359766-28-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 100 percent / sodium hydride / dimethylformamide / 0.5 h / 20 °C

2.1: 93 percent / sodium cyanoborohydride; HCl; 3 Angstroem molecular sieve / tetrahydrofuran; diethyl ether / 0.17 h

3.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

4.1: 66 percent / diethyl ether / 0.5 h / -78 °C

5.1: 100 percent / p-toluenesulfonic acid monohydrate / Pd/C / methanol; H₂O / 12 h / 70 °C

6.1: dibuthyltin oxide / benzene; methanol / 12 h / 70 °C

6.2: 100 percent / Et₃N / dioxane / 0.5 h / 20 °C

7.1: 94 percent / N-ethyl-diisopropylamine / CH₂Cl₂ / 0.5 h

8.1: 100 percent / H₂ / Pd(OH)2 / ethanol / 24 h / 20 °C / 760.05 Torr

9.1: 99 percent / diisopropylethylamine / dimethylformamide / 0.75 h / 20 °C

10.1: 75 percent / 2,6-lutidine / CH₂Cl₂ / 24 h / 20 °C

11.1: 95 percent / Bu₄NF; BF₃*OEt₂ / acetonitrile; tetrahydrofuran / 1 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/ol010089t

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (2S,3R,4R,5R,6R)-5-hydroxy-6-hydroxymethyl-4-methanesulfonyloxy-5-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester (359766-28-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dibuthyltin oxide / benzene; methanol / 12 h / 70 °C

1.2: 100 percent / Et₃N / dioxane / 0.5 h / 20 °C

2.1: 94 percent / N-ethyl-diisopropylamine / CH₂Cl₂ / 0.5 h

3.1: 100 percent / H₂ / Pd(OH)2 / ethanol / 24 h / 20 °C / 760.05 Torr

4.1: 99 percent / diisopropylethylamine / dimethylformamide / 0.75 h / 20 °C

5.1: 75 percent / 2,6-lutidine / CH₂Cl₂ / 24 h / 20 °C

6.1: 95 percent / Bu₄NF; BF₃*OEt₂ / acetonitrile; tetrahydrofuran / 1 h / 20 °C

With 2,6-dimethylpyridine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/ol010089t

upstream raw materials:

Benzoic acid (2S,3R,4R,5R,6R)-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-4-methanesulfonyloxy-5-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside

benzoyl chloride

(2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol

Downstream raw materials:

Benzoic acid (2S,3R,4R,5R,6R)-5-hydroxy-4-methanesulfonyloxy-5-methyl-2-triisopropylsilanyloxy-6-((1E,3E,7E,9E)-(5R,11S)-5,7,11-trimethyl-trideca-1,3,7,9-tetraenyl)-tetrahydro-pyran-3-yl ester

Benzoic acid (2S,3R,4R,5R,6R)-5-hydroxy-4-methanesulfonyloxy-5-methyl-6-[(E)-3-(1-phenyl-1H-tetrazole-5-sulfonyl)-propenyl]-2-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

Benzoic acid (2S,3R,4R,5R,6R)-5-hydroxy-4-methanesulfonyloxy-5-methyl-6-[(E)-3-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-propenyl]-2-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

Benzoic acid (1R,2R,4S,5R,6S)-1-methyl-4-triisopropylsilanyloxy-2-((1E,3E,7E,9E)-(5R,11S)-5,7,11-trimethyl-trideca-1,3,7,9-tetraenyl)-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester