(3'aS,4'S,5'S,6'S)-4',5'-bis(benzyloxy)-6'-(benzyloxymethyl)dispiro[cyclopropane-1,2'-(hexahydropyrrolo[1,2-b]isoxazole)-3',1''-cyclopropane]

Base Information

• Chemical Name: (3'aS,4'S,5'S,6'S)-4',5'-bis(benzyloxy)-6'-(benzyloxymethyl)dispiro[cyclopropane-1,2'-(hexahydropyrrolo[1,2-b]isoxazole)-3',1''-cyclopropane]
• CAS No.: 1032166-38-3
• Molecular Formula: C₃₂H₃₅NO₄
• Molecular Weight: 497.634

Synonyms:(3'aS,4'S,5'S,6'S)-4',5'-bis(benzyloxy)-6'-(benzyloxymethyl)dispiro[cyclopropane-1,2'-(hexahydropyrrolo[1,2-b]isoxazole)-3',1''-cyclopropane]

Chemical Property of (3'aS,4'S,5'S,6'S)-4',5'-bis(benzyloxy)-6'-(benzyloxymethyl)dispiro[cyclopropane-1,2'-(hexahydropyrrolo[1,2-b]isoxazole)-3',1''-cyclopropane]

Chemical Property:

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Technology Process of (3'aS,4'S,5'S,6'S)-4',5'-bis(benzyloxy)-6'-(benzyloxymethyl)dispiro[cyclopropane-1,2'-(hexahydropyrrolo[1,2-b]isoxazole)-3',1''-cyclopropane]

There total 1 articles about (3'aS,4'S,5'S,6'S)-4',5'-bis(benzyloxy)-6'-(benzyloxymethyl)dispiro[cyclopropane-1,2'-(hexahydropyrrolo[1,2-b]isoxazole)-3',1''-cyclopropane] 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: 90.0%

bicyclopropylidene (27567-82-4) + (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide (537030-19-6) → (3'aS,4'S,5'S,6'S)-4',5'-bis(benzyloxy)-6'-(benzyloxymethyl)dispiro[cyclopropane-1,2'-(hexahydropyrrolo[1,2-b]isoxazole)-3',1''-cyclopropane] (1032166-38-3)

Guidance literature:

In toluene; at 60 ℃; for 48h; Inert atmosphere;

DOI:10.1002/ejoc.200700912

Reference yield: 95.0%

(3'aS,4'S,5'S,6'S)-4',5'-bis(benzyloxy)-6'-(benzyloxymethyl)dispiro[cyclopropane-1,2'-(hexahydropyrrolo[1,2-b]isoxazole)-3',1''-cyclopropane] (1032166-38-3) → (1'R,2'R,3'R,8'aR)-1',2'-bis(benzyloxy)-3'-[(benzyloxy)methyl]spiro[cyclopropane-1,8'-(hexahydroindolizin)]-7'(1'H)-one (1032166-81-6)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; at 120 ℃; for 12h; Inert atmosphere;

DOI:10.1002/ejoc.200700912

Reference yield: 94.0%

(3'aS,4'S,5'S,6'S)-4',5'-bis(benzyloxy)-6'-(benzyloxymethyl)dispiro[cyclopropane-1,2'-(hexahydropyrrolo[1,2-b]isoxazole)-3',1''-cyclopropane] (1032166-38-3) + trifluoroacetic acid (76-05-1) → 1-[(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-1-(trifluoroacetyl)pyrrolidin-2-yl]cyclopropanecarboxylic acid (1158917-72-6)

Guidance literature:

In toluene; at 110 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1021/jo9004684

upstream raw materials:

bicyclopropylidene

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide

Downstream raw materials:

1'-{(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]pyrrolidin-2-yl}-1,1'-bicyclopropyl-1-ol

(1'R,2'R,3'R,8'aR)-1',2'-bis(benzyloxy)-3'-[(benzyloxy)methyl]spiro[cyclopropane-1,8'-(hexahydroindolizin)]-7'(1'H)-one

1-[(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-1-(trifluoroacetyl)pyrrolidin-2-yl]cyclopropanecarboxylic acid

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