(1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate

Base Information

• Chemical Name: (1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate
• CAS No.: 251085-88-8
• Molecular Formula: C₁₄H₁₃F₃O₆S
• Molecular Weight: 366.315
• Mol file: 251085-88-8.mol

Synonyms:(1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate

Chemical Property of (1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate

There total 3 articles about (1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate 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: 87.0%

1,6-anhydro-2-O-benzyl-3-deoxy-β-D-erythro-hexopyrano-4-ulose (123823-24-5) + N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide (145100-51-2) → (1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate (251085-88-8)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃;

DOI:10.1039/a905310g

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → (1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate (251085-88-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / 25 °C

2: 87 percent / LiHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C

With triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1: Addition / 2: Substitution;

DOI:10.1039/a905310g

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → (1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate (251085-88-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / Et₃N

2.1: n-BuLi; (Me₃Si)2NH; HMPA / tetrahydrofuran; hexane / 2 h / -78 °C

2.2: 85 percent / tetrahydrofuran; hexane / -78 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane;

DOI:10.1016/j.tetasy.2004.11.048

upstream raw materials:

1,6-anhydro-2-O-benzyl-3-deoxy-β-D-erythro-hexopyrano-4-ulose

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

benzyl alcohol

Downstream raw materials:

(2S,4R)-2-[(R)-((1S,2S,3S,4R,5R)-4-Benzyloxy-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-2-[(R)-((1S,2S,3S,4R,5R)-4-Benzyloxy-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

(-)-((1S,4R,5R)-4-(benzyloxy)-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl)((4aR,8R,8aR)-2,2-di-tert-butyl-8-((triisopropylsilyl)oxy)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl)methanone

(2S,4R)-2-[(R)-((1S,4R,5R)-4-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-en-2-yl)-hydroxy-methyl]-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester