(3aR,5R,6R,7S,7aR)-5-((benzoyloxy)methyl)-2-(pent-4-en-1-yloxy)-2-phenyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl dibenzoate

Base Information

• Chemical Name: (3aR,5R,6R,7S,7aR)-5-((benzoyloxy)methyl)-2-(pent-4-en-1-yloxy)-2-phenyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl dibenzoate
• CAS No.: 297747-11-6
• Molecular Formula: C₃₉H₃₆O₁₀
• Molecular Weight: 664.709
• Mol file: 297747-11-6.mol

Synonyms:(3aR,5R,6R,7S,7aR)-5-((benzoyloxy)methyl)-2-(pent-4-en-1-yloxy)-2-phenyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl dibenzoate

Chemical Property of (3aR,5R,6R,7S,7aR)-5-((benzoyloxy)methyl)-2-(pent-4-en-1-yloxy)-2-phenyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl dibenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5R,6R,7S,7aR)-5-((benzoyloxy)methyl)-2-(pent-4-en-1-yloxy)-2-phenyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl dibenzoate

There total 12 articles about (3aR,5R,6R,7S,7aR)-5-((benzoyloxy)methyl)-2-(pent-4-en-1-yloxy)-2-phenyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl dibenzoate 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: 94.0%

n-Pent-4-enyl alcohol (821-09-0) + C43H38O11 → (3aR,5R,6R,7S,7aR)-5-((benzoyloxy)methyl)-2-(pent-4-en-1-yloxy)-2-phenyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl dibenzoate (297747-11-6)

Guidance literature:

n-Pent-4-enyl alcohol; C₄₃H₃₈O₁₁; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere; Molecular sieve;

With C₂F₆NO₄S₂^(1-)*Au⁽¹⁺⁾*C₂₆H₃₅O₂P; In dichloromethane; at 20 ℃; for 3h; Reagent/catalyst; Inert atmosphere; Molecular sieve;

DOI:10.1021/acs.orglett.9b03851

Reference yield: 86.0%

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) + n-Pent-4-enyl alcohol (821-09-0) → (3aR,5R,6R,7S,7aR)-5-((benzoyloxy)methyl)-2-(pent-4-en-1-yloxy)-2-phenyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl dibenzoate (297747-11-6)

Guidance literature:

With 2,6-dimethylpyridine; tetra-(n-butyl)ammonium iodide; In dichloromethane; for 24h; Inert atmosphere; Reflux;

DOI:10.1021/jacs.9b03285

Reference yield: 85.0%

n-Pent-4-enyl alcohol (821-09-0) + (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-((3-oxo-5-phenylpent-4-ynoyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate → (3aR,5R,6R,7S,7aR)-5-((benzoyloxy)methyl)-2-(pent-4-en-1-yloxy)-2-phenyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl dibenzoate (297747-11-6)

Guidance literature:

With trifluoromethanesulfonyloxy(triphenylphosphine)gold(I); In dichloromethane; at 20 ℃; for 4h; Molecular sieve; Inert atmosphere;

DOI:10.1021/acs.joc.9b01582

upstream raw materials:

2,3,4,6-tetra-O-benzoylglucosyl bromide

n-Pent-4-enyl alcohol

1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose

2,3,4,6-tetra-O-Bz-β-D-glucopyranosyl bromide

Downstream raw materials:

1,3,4,5-tetra-O-benzyl-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-D-myo-inositol

2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl fluoride

C₆₄H₅₈O₁₅

C₆₄H₅₈O₁₅

Refernces

• 1、 Liu, Rongkun,Li, Xiaoqian,Li, Xiaona,Wang, Jiazhe,Yang, You. "Gold(I)-Catalyzed Intermolecular Rearrangement Reaction of Glycosyl Alkynoic β-Ketoesters for the Synthesis of 4- O-Glycosylated 2-Pyrones". . p. 14141 - 14150. Retrieved 2019/10/17.
• 2、 Thadke, Shivaji A.,Hotha, Srinivas. "Efficient synthesis of oligosaccharyl 1,2-O-orthoesters from n-pentenyl glycosides and application to the pentaarabinofuranoside of the mycobacterial cell surface". . p. 9914 - 9920. Retrieved 2015/01/08.