Benzoic acid (3S,4R,5R,6R)-2-((R)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (3S,4R,5R,6R)-2-((R)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester
• CAS No.: 119007-05-5
• Molecular Formula: C₂₈H₄₀O₉Si
• Molecular Weight: 548.706

Synonyms:Benzoic acid (3S,4R,5R,6R)-2-((R)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (3S,4R,5R,6R)-2-((R)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of Benzoic acid (3S,4R,5R,6R)-2-((R)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester

There total 12 articles about Benzoic acid (3S,4R,5R,6R)-2-((R)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-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: 11.2%

Benzoic acid (R)-2-((E)-3-benzyloxy-propenyl)-4-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydro-2H-pyran-3-yl ester (118893-67-7) → Benzoic acid (3S,4R,5R)-2-((S)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester (118893-68-8,119007-05-5) + Benzoic acid (3S,4R,5R,6R)-2-((R)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester (119007-05-5) + Benzoic acid (3S,4R,5R,6S)-2-((R)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester (118893-68-8)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; tert-butyl alcohol; for 18h; Yield given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/ja00188a038

Reference yield: 11.2%

Benzoic acid (R)-2-((E)-3-benzyloxy-propenyl)-4-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydro-2H-pyran-3-yl ester (118893-67-7) → Benzoic acid (3S,4R,5R)-2-((S)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester (118893-68-8,119007-05-5) + Benzoic acid (3S,4R,5R,6R)-2-((R)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester (119007-05-5) + Benzoic acid (3S,4R,5R,6S)-2-((R)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester (118893-68-8)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; tert-butyl alcohol; for 18h; Yield given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/ja00188a038

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → Benzoic acid (3S,4R,5R)-2-((S)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester (118893-68-8,119007-05-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 86.8 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2: 11.2 percent / osmium tetroxide, N-methylmorpholine N-oxide / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 18 h / Ambient temperature

With 2,6-dimethylpyridine; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/ja00188a038

upstream raw materials:

Benzoic acid (R)-2-((E)-3-benzyloxy-propenyl)-4-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydro-2H-pyran-3-yl ester

4-benzyloxycrotonaldehyde

t-butyldimethylsiyl triflate

1-methoxy-3-((tert-butyldimethylsilyl)oxy)-4-(benzoyloxy)-1,3-butadiene

Downstream raw materials:

Benzoic acid (3S,4R,5R)-2-((R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester

Benzoic acid (3aR,5R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-5-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester

Benzoic acid (3aR,5R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-5-((4S,5R)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester

Benzoic acid (3aR,5R,6S,7S,7aR)-5-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester

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