(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R)-3,4-diacetoxy-5-amino-6-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R)-3,4-diacetoxy-5-amino-6-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 116246-53-8
• Molecular Formula: C₄₈H₆₁N₃O₂₃
• Molecular Weight: 1048.02

Synonyms:

Chemical Property of (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R)-3,4-diacetoxy-5-amino-6-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R)-3,4-diacetoxy-5-amino-6-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 8 articles about (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R)-3,4-diacetoxy-5-amino-6-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl 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:

N-benzyloxycarbonyl-L-serine benzyl ester (21209-51-8) → (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R)-3,4-diacetoxy-5-amino-6-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (116246-53-8,116299-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / molecular sives AW/Me₃SiSO₂CF₃ / 1,2-dichloro-ethane / 0.67 h / -15 °C

2: H₂ / Lindlar / methanol / 6.5 h / 40 °C

With molecular sives AW; hydrogen; trimethyl((trifluoromethyl)sulfonyl)silane; Lindlar's catalyst; In methanol; 1,2-dichloro-ethane;

DOI:10.1016/S0008-6215(00)90853-X

Reference yield:

O--(2->6)-O-(3,4-di-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl)-(1->3)-N-(benzoylcarbonyl)-L-serine benzyl ester → (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R)-3,4-diacetoxy-5-amino-6-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (116246-53-8,116299-44-6)

Guidance literature:

With hydrogen; Lindlar's catalyst; In methanol; at 40 ℃; for 6.5h;

DOI:10.1016/S0008-6215(00)90853-X

Reference yield:

Allyl-2-azido-2-desoxy-β-D-galactopyranosid (90405-18-8) → (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R)-3,4-diacetoxy-5-amino-6-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (116246-53-8,116299-44-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 41 percent / molecular sives 4A/AgOSO₂CF₃ / tetrahydrofuran / 20 h / 20 °C

2: 98 percent / pyridine / 12 h / 20 °C

3: 79 percent / PdCl₂/AcONa / acetic acid; H₂O / 12 h / 20 °C

4: 70 percent / K₂CO₃ / CH₂Cl₂ / 3 h / 20 °C

5: 82 percent / molecular sives AW/Me₃SiSO₂CF₃ / 1,2-dichloro-ethane / 0.67 h / -15 °C

6: H₂ / Lindlar / methanol / 6.5 h / 40 °C

With molecular sives 4A; molecular sives AW; hydrogen; sodium acetate; silver trifluoromethanesulfonate; potassium carbonate; trimethyl((trifluoromethyl)sulfonyl)silane; palladium dichloride; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane;

DOI:10.1016/S0008-6215(00)90853-X

upstream raw materials:

N-benzyloxycarbonyl-L-serine benzyl ester

Allyl-2-azido-2-desoxy-β-D-galactopyranosid

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

allyl O--(2->6)-3,4-di-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside

Downstream raw materials:

O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine

O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(benzyloxycarbonyl)-L-serine benzyl ester

O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-β-D-galactopyranosyl)-(1->3)-N-(benzyloxycarbonyl)-L-serine benzyl ester

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