(3R,3aS,4R,5S,6S,6aR)-1-Benzyl-5-benzyloxy-4,6-dihydroxy-hexahydro-cyclopenta[c]isoxazole-3-carboxylic acid ethyl ester

Base Information

• Chemical Name: (3R,3aS,4R,5S,6S,6aR)-1-Benzyl-5-benzyloxy-4,6-dihydroxy-hexahydro-cyclopenta[c]isoxazole-3-carboxylic acid ethyl ester
• CAS No.: 364336-46-9
• Molecular Formula: C₂₃H₂₇NO₆
• Molecular Weight: 413.47
• Mol file: 364336-46-9.mol

Synonyms:(3R,3aS,4R,5S,6S,6aR)-1-Benzyl-5-benzyloxy-4,6-dihydroxy-hexahydro-cyclopenta[c]isoxazole-3-carboxylic acid ethyl ester

Chemical Property of (3R,3aS,4R,5S,6S,6aR)-1-Benzyl-5-benzyloxy-4,6-dihydroxy-hexahydro-cyclopenta[c]isoxazole-3-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3aS,4R,5S,6S,6aR)-1-Benzyl-5-benzyloxy-4,6-dihydroxy-hexahydro-cyclopenta[c]isoxazole-3-carboxylic acid ethyl ester

There total 2 articles about (3R,3aS,4R,5S,6S,6aR)-1-Benzyl-5-benzyloxy-4,6-dihydroxy-hexahydro-cyclopenta[c]isoxazole-3-carboxylic acid ethyl 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: 65.0%

N-benzylhydroxylamine hydrochloride (29601-98-7) + (E)-3-((2R,3R,4R)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-acrylic acid ethyl ester → (3R,3aS,4R,5S,6S,6aR)-1-Benzyl-5-benzyloxy-4,6-dihydroxy-hexahydro-cyclopenta[c]isoxazole-3-carboxylic acid ethyl ester (364336-46-9)

Guidance literature:

With sodium acetate; In ethanol; Heating;

DOI:10.1016/S0040-4039(01)00877-2

Reference yield:

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate (108788-49-4) → (3R,3aS,4R,5S,6S,6aR)-1-Benzyl-5-benzyloxy-4,6-dihydroxy-hexahydro-cyclopenta[c]isoxazole-3-carboxylic acid ethyl ester (364336-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / TFA / H₂O / 2.5 h / 0 - 20 °C

2: 65 percent / Sodium acetate / aq. ethanol / Heating

With sodium acetate; trifluoroacetic acid; In ethanol; water;

DOI:10.1016/S0040-4039(01)00877-2

Reference yield:

(3R,3aS,4R,5S,6S,6aR)-1-Benzyl-5-benzyloxy-4,6-dihydroxy-hexahydro-cyclopenta[c]isoxazole-3-carboxylic acid ethyl ester (364336-46-9) → Acetic acid (3R,3aS,4R,5S,6S,6aR)-4-acetoxy-3-acetoxymethyl-1-benzyl-5-benzyloxy-hexahydro-cyclopenta[c]isoxazol-6-yl ester (364336-49-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / LAH / tetrahydrofuran / 1 h / 0 °C

2: 81 percent / pyridine; DMAP / 18 h / 20 °C

With pyridine; dmap; lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)00877-2

upstream raw materials:

N-benzylhydroxylamine hydrochloride

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

Downstream raw materials:

Acetic acid (3R,3aS,4R,5S,6S,6aR)-4-acetoxy-3-acetoxymethyl-1-benzyl-5-benzyloxy-hexahydro-cyclopenta[c]isoxazol-6-yl ester