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

Base Information

Chemical Name:Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-benzyloxycarbonylamino-tetrahydro-pyran-4-yl ester
CAS No.:214473-43-5
Molecular Formula:C₂₂H₂₈N₂O₁₀
Molecular Weight:480.472
Hs Code.:

Synonyms:Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-benzyloxycarbonylamino-tetrahydro-pyran-4-yl ester

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

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

There total 7 articles about Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-benzyloxycarbonylamino-tetrahydro-pyran-4-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: 82.0%

: 102987-95-1
C₁₅H₂₀N₂O₈

: 100-51-6,185532-71-2
benzyl alcohol

: 214473-43-5
Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-benzyloxycarbonylamino-tetrahydro-pyran-4-yl ester

Guidance literature:: C₁₅H₂₀N₂O₈; With pyridine N-oxide; 3 A molecular sieve; iodine; In acetonitrile; at 20 ℃; for 0.0833333h;

benzyl alcohol; In acetonitrile; at 70 ℃;
DOI:10.1021/ol0616788

Reference yield:

: 6205-69-2
2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide

: 214473-43-5
Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-benzyloxycarbonylamino-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: H₂; Et₃N / Pd/C / ethyl acetate / 0.5 h

2.1: 1.50 g / ethyl acetate / 0.5 h / 20 °C

3.1: 81 percent / triphosgene; Et₃N / CH₂Cl₂ / 2 h / 20 °C

4.1: pyridine N-oxide; I₂; 3 Angstroem molecular sieves / acetonitrile / 0.08 h / 20 °C

4.2: 82 percent / acetonitrile / 70 °C

With pyridine N-oxide; bis(trichloromethyl) carbonate; 3 A molecular sieve; hydrogen; iodine; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/ol0616788

Reference yield:

: 3068-34-6
Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

: 214473-43-5
Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-benzyloxycarbonylamino-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaN₃; nBu₄NHSO₄; aq. NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

2.1: H₂; Et₃N / Pd/C / ethyl acetate / 0.5 h

3.1: 1.50 g / ethyl acetate / 0.5 h / 20 °C

4.1: 81 percent / triphosgene; Et₃N / CH₂Cl₂ / 2 h / 20 °C

5.1: pyridine N-oxide; I₂; 3 Angstroem molecular sieves / acetonitrile / 0.08 h / 20 °C

5.2: 82 percent / acetonitrile / 70 °C

With pyridine N-oxide; sodium azide; bis(trichloromethyl) carbonate; 3 A molecular sieve; hydrogen; iodine; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/ol0616788