(3S,6R,8R,9R,10S,11R)-ethyl 9,10,11-tris(benzyloxy)-8-(benzyloxymethyl)-1,7-dioxa-2-azaspiro[5.5]undecane-3-carboxylate

Base Information

• Chemical Name: (3S,6R,8R,9R,10S,11R)-ethyl 9,10,11-tris(benzyloxy)-8-(benzyloxymethyl)-1,7-dioxa-2-azaspiro[5.5]undecane-3-carboxylate
• CAS No.: 1268670-52-5
• Molecular Formula: C₄₀H₄₅NO₈
• Molecular Weight: 667.799

Synonyms:(3S,6R,8R,9R,10S,11R)-ethyl 9,10,11-tris(benzyloxy)-8-(benzyloxymethyl)-1,7-dioxa-2-azaspiro[5.5]undecane-3-carboxylate

Chemical Property of (3S,6R,8R,9R,10S,11R)-ethyl 9,10,11-tris(benzyloxy)-8-(benzyloxymethyl)-1,7-dioxa-2-azaspiro[5.5]undecane-3-carboxylate

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Technology Process of (3S,6R,8R,9R,10S,11R)-ethyl 9,10,11-tris(benzyloxy)-8-(benzyloxymethyl)-1,7-dioxa-2-azaspiro[5.5]undecane-3-carboxylate

There total 1 articles about (3S,6R,8R,9R,10S,11R)-ethyl 9,10,11-tris(benzyloxy)-8-(benzyloxymethyl)-1,7-dioxa-2-azaspiro[5.5]undecane-3-carboxylate 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: 80.0%

(6R,8R,9R,10S,11R)-ethyl 9,10,11-tris(benzyloxy)-8-(benzyloxymethyl)-1,7-dioxa-2-azaspiro[5.5]undec-2-ene-3-carboxylate (1268670-51-4) → (3S,6R,8R,9R,10S,11R)-ethyl 9,10,11-tris(benzyloxy)-8-(benzyloxymethyl)-1,7-dioxa-2-azaspiro[5.5]undecane-3-carboxylate (1268670-52-5)

Guidance literature:

(6R,8R,9R,10S,11R)-ethyl 9,10,11-tris(benzyloxy)-8-(benzyloxymethyl)-1,7-dioxa-2-azaspiro[5.5]undec-2-ene-3-carboxylate; With sodium cyanoborohydride; In acetic acid; at 0 - 20 ℃; for 24h; Inert atmosphere;

With triethylamine; In chloroform; for 0.5h; stereoselective reaction; Reflux;

DOI:10.1016/j.carres.2010.12.001

Reference yield: 50.0%

di-tert-butyl dicarbonate (24424-99-5) + (3S,6R,8R,9R,10S,11R)-ethyl 9,10,11-tris(benzyloxy)-8-(benzyloxymethyl)-1,7-dioxa-2-azaspiro[5.5]undecane-3-carboxylate (1268670-52-5) → (3S,6R,8R,9R,10S,11R)-2-tert-butyl 3-ethyl 9,10,11-tris(benzyloxy)-8-(benzyloxymethyl)-1,7-dioxa-2-azaspiro[5.5]undecane-2,3-dicarboxylate (1268670-53-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.carres.2010.12.001

upstream raw materials:

(6R,8R,9R,10S,11R)-ethyl 9,10,11-tris(benzyloxy)-8-(benzyloxymethyl)-1,7-dioxa-2-azaspiro[5.5]undec-2-ene-3-carboxylate

Downstream raw materials:

(3S,6R,8R,9R,10S,11R)-2-tert-butyl 3-ethyl 9,10,11-tris(benzyloxy)-8-(benzyloxymethyl)-1,7-dioxa-2-azaspiro[5.5]undecane-2,3-dicarboxylate

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