tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate

Base Information

• Chemical Name: tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate
• CAS No.: 1252027-19-2
• Molecular Formula: C₃₂H₃₇NO₇
• Molecular Weight: 547.648

Synonyms:tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate

Chemical Property of tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate

Chemical Property:

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Technology Process of tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate

There total 1 articles about tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate 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%

tert-butyl [2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4-O-(1-naphthyl)methyl-L-iditol]uronate (1252027-35-2) → tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate (1252027-19-2)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetonitrile; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2010.07.055

Reference yield: 97.0%

tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate (1252027-19-2) → (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronic acid (1252027-50-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 1h;

DOI:10.1016/j.tet.2010.07.055

Reference yield: 80.0%

phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside (1207750-80-8) + tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate (1252027-19-2) → (2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate] (1252027-38-5)

Guidance literature:

phenyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α,β-D-glucopyranoside; tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate; In diethyl ether; dichloromethane; at -30 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With Me₂S₂-Tf₂O; In diethyl ether; dichloromethane; for 5h; Inert atmosphere;

DOI:10.1016/j.tet.2010.07.055

upstream raw materials:

tert-butyl [2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4-O-(1-naphthyl)methyl-L-iditol]uronate

Downstream raw materials:

(2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-[tert-butyl (2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronate]

(2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-L-iditol)uronic acid

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