(2R,4R,5S,6R)-5-Benzoyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-((1S,2S)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,4R,5S,6R)-5-Benzoyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-((1S,2S)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 102650-50-0
• Molecular Formula: C₄₅H₅₀O₁₃Si
• Molecular Weight: 826.97
• Mol file: 102650-50-0.mol

Synonyms:

Chemical Property of (2R,4R,5S,6R)-5-Benzoyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-((1S,2S)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,5S,6R)-5-Benzoyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-((1S,2S)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 7 articles about (2R,4R,5S,6R)-5-Benzoyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-((1S,2S)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic 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:

Benzoic acid (2S,3R,4S,6S)-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester (102650-44-2) → (2R,4R,5S,6R)-5-Benzoyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-((1S,2S)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (102650-50-0,113974-08-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 87 percent / Pd(OH)2/C / ethyl acetate; methanol

2: 90 percent / CrO₃, pyridine

3: KHMDS

4: 87 percent / osmium tetraoxide / pyridine

5: lithium triethylborohydride / tetrahydrofuran

6: DMAP / CH₂Cl₂

7: 1.) RuO₂, NaIO₄, NaHCO₃

With pyridine; chromium(VI) oxide; dmap; ruthenium(IV) oxide; sodium periodate; osmium(VIII) oxide; potassium hexamethylsilazane; lithium triethylborohydride; sodium hydrogencarbonate; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate;

DOI:10.1021/jo00363a047

Reference yield:

Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester (102650-45-3) → (2R,4R,5S,6R)-5-Benzoyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-((1S,2S)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (102650-50-0,113974-08-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / CrO₃, pyridine

2: KHMDS

3: 87 percent / osmium tetraoxide / pyridine

4: lithium triethylborohydride / tetrahydrofuran

5: DMAP / CH₂Cl₂

6: 1.) RuO₂, NaIO₄, NaHCO₃

With pyridine; chromium(VI) oxide; dmap; ruthenium(IV) oxide; sodium periodate; osmium(VIII) oxide; potassium hexamethylsilazane; lithium triethylborohydride; sodium hydrogencarbonate; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jo00363a047

Reference yield:

Benzoic acid (2R,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-formyl-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester (102650-46-4,114027-47-3) → (2R,4R,5S,6R)-5-Benzoyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-((1S,2S)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (102650-50-0,113974-08-6)

Guidance literature:

Multi-step reaction with 5 steps

1: KHMDS

2: 87 percent / osmium tetraoxide / pyridine

3: lithium triethylborohydride / tetrahydrofuran

4: DMAP / CH₂Cl₂

5: 1.) RuO₂, NaIO₄, NaHCO₃

With dmap; ruthenium(IV) oxide; sodium periodate; osmium(VIII) oxide; potassium hexamethylsilazane; lithium triethylborohydride; sodium hydrogencarbonate; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jo00363a047

upstream raw materials:

diazomethane

C₄₇H₅₀O₁₂Si

Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester

Benzoic acid (2R,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-formyl-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester

Downstream raw materials:

(2S,4S,5S,6R)-5-Benzoyloxy-4-hydroxy-2-methoxy-6-((1R,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,4S,5S,6R)-4-Benzoyloxy-5-hydroxy-2-methoxy-6-((1R,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester