Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-hydroxy-ethoxy)-6-propoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-hydroxy-ethoxy)-6-propoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 180154-26-1
• Molecular Formula: C₃₄H₄₉NO₁₆
• Molecular Weight: 727.76

Synonyms:Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-hydroxy-ethoxy)-6-propoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-hydroxy-ethoxy)-6-propoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-hydroxy-ethoxy)-6-propoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

There total 4 articles about Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-hydroxy-ethoxy)-6-propoxy-tetrahydro-pyran-3-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:

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-oxo-ethoxy)-6-propoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-hydroxy-ethoxy)-6-propoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (180154-26-1)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 0.333333h; Yield given; Ambient temperature;

DOI:10.1021/ja960274f

Reference yield:

N-((2R,3R,4R,5S,6R)-4-Allyloxy-6-benzyloxymethyl-5-hydroxy-2-propoxy-tetrahydro-pyran-3-yl)-acetamide → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-hydroxy-ethoxy)-6-propoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (180154-26-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 38 percent / TMSOTf / CH₂Cl₂ / 18 h / Ambient temperature

2: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 5 min, 2.) CH₂Cl₂, a) -78 deg C, 1 h, b) RT, 1 h

3: aq. NaBH₄ / ethanol / 0.33 h / Ambient temperature

With sodium tetrahydroborate; dimethylsulfide; trimethylsilyl trifluoromethanesulfonate; ozone; In ethanol; dichloromethane;

DOI:10.1021/ja960274f

Reference yield:

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-allyloxy-2-benzyloxymethyl-6-propoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (180154-25-0) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-hydroxy-ethoxy)-6-propoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (180154-26-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 5 min, 2.) CH₂Cl₂, a) -78 deg C, 1 h, b) RT, 1 h

2: aq. NaBH₄ / ethanol / 0.33 h / Ambient temperature

With sodium tetrahydroborate; dimethylsulfide; ozone; In ethanol;

DOI:10.1021/ja960274f

upstream raw materials:

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-allyloxy-2-benzyloxymethyl-6-propoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

Downstream raw materials:

C₆₉H₈₆N₂O₁₉

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