4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-benzyloxycarbonyl-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

Base Information

• Chemical Name: 4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-benzyloxycarbonyl-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester
• CAS No.: 309761-70-4
• Molecular Formula: C₅₂H₇₃NO₂₄
• Molecular Weight: 1096.14

Synonyms:4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-benzyloxycarbonyl-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

Chemical Property of 4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-benzyloxycarbonyl-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

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Technology Process of 4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-benzyloxycarbonyl-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

There total 3 articles about 4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-benzyloxycarbonyl-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl 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: 38.0%

(1S,2S,4R,5S)-4-((S)-1-Benzyloxycarbonyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester (309761-66-8) + Trichloro-acetic acid (3R,4R,5R,6R)-5-acetoxy-6-acetoxymethyl-3-acetylamino-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl ester → 4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-benzyloxycarbonyl-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester (309761-70-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; Heating;

DOI:10.1016/S0960-894X(00)00428-5

Reference yield:

(S)-2-(trifluoromethanesulphonyloxy)propionic acid benzyl ester (93836-48-7) → 4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-benzyloxycarbonyl-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester (309761-70-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / benzene / Heating

1.2: 76 percent / Bu₄NI / benzene

2.1: 38 percent / TMSOTf / CH₂Cl₂ / Heating

With trimethylsilyl trifluoromethanesulfonate; di(n-butyl)tin oxide; In dichloromethane; benzene; 1.1: stannylation / 1.2: Etherification / 2.1: glycosylation;

DOI:10.1016/S0960-894X(00)00428-5

Reference yield:

(1S,2S,4R,5S)-4,5-Dihydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester (221344-09-8) → 4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-benzyloxycarbonyl-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester (309761-70-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / benzene / Heating

1.2: 76 percent / Bu₄NI / benzene

2.1: 38 percent / TMSOTf / CH₂Cl₂ / Heating

With trimethylsilyl trifluoromethanesulfonate; di(n-butyl)tin oxide; In dichloromethane; benzene; 1.1: stannylation / 1.2: Etherification / 2.1: glycosylation;

DOI:10.1016/S0960-894X(00)00428-5

upstream raw materials:

(1S,2S,4R,5S)-4-((S)-1-Benzyloxycarbonyl-ethoxy)-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

(S)-2-(trifluoromethanesulphonyloxy)propionic acid benzyl ester

(1S,2S,4R,5S)-4,5-Dihydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

Downstream raw materials:

4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-carboxy-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

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