Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-(6-benzyloxycarbonylamino-hexyloxy)-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-(6-benzyloxycarbonylamino-hexyloxy)-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 189108-66-5
• Molecular Formula: C₄₀H₅₆N₂O₁₉
• Molecular Weight: 868.887

Synonyms:

Chemical Property of Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-(6-benzyloxycarbonylamino-hexyloxy)-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-(6-benzyloxycarbonylamino-hexyloxy)-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

There total 7 articles about Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-(6-benzyloxycarbonylamino-hexyloxy)-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl 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-6-amino-1-hexanol (17996-12-2) → Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-(6-benzyloxycarbonylamino-hexyloxy)-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (189108-66-5)

Guidance literature:

Multi-step reaction with 3 steps

1: ZnBr₂

2: NiCl₂*6H₂O, H₃BO₃, NaBH₄ / ethanol / 1 h

3: 2 h

With sodium tetrahydroborate; boric acid; nickel dichloride; zinc dibromide; In ethanol;

DOI:10.1016/S0008-6215(96)00309-6

Reference yield:

Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-5-azido-6-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester → Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-(6-benzyloxycarbonylamino-hexyloxy)-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (189108-66-5)

Guidance literature:

Multi-step reaction with 4 steps

1: LiBr / acetonitrile / 3 h

2: ZnBr₂

3: NiCl₂*6H₂O, H₃BO₃, NaBH₄ / ethanol / 1 h

4: 2 h

With sodium tetrahydroborate; boric acid; lithium bromide; nickel dichloride; zinc dibromide; In ethanol; acetonitrile;

DOI:10.1016/S0008-6215(96)00309-6

Reference yield:

4,6-di-O-acetyl-2-azido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl bromide (85640-94-4) → Acetic acid (2R,3R,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-(6-benzyloxycarbonylamino-hexyloxy)-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (189108-66-5)

Guidance literature:

Multi-step reaction with 3 steps

1: ZnBr₂

2: NiCl₂*6H₂O, H₃BO₃, NaBH₄ / ethanol / 1 h

3: 2 h

With sodium tetrahydroborate; boric acid; nickel dichloride; zinc dibromide; In ethanol;

DOI:10.1016/S0008-6215(96)00309-6

upstream raw materials:

acetic anhydride

N-benzyloxycarbonyl-6-amino-1-hexanol

4,6-di-O-acetyl-2-azido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl bromide

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1[*]3)-4,6-di-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride

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