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

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(2-trimethylsilanyl-acetylamino)-tetrahydro-pyran-4-yl ester
• CAS No.: 172688-21-0
• Molecular Formula: C₁₉H₃₁NO₁₀Si
• Molecular Weight: 461.541
• Mol file: 172688-21-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(2-trimethylsilanyl-acetylamino)-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:

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1) + Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(2-trimethylsilanyl-acetylamino)-tetrahydro-pyran-4-yl ester (172688-21-0) + Trimethylsilanyl-acetic acid (2R,3S,4R,5R,6R)-3,4,6-triacetoxy-5-acetylamino-tetrahydro-pyran-2-ylmethyl ester + Trimethylsilanyl-acetic acid (2R,3S,4R,5R,6R)-3,4,6-triacetoxy-5-(2-trimethylsilanyl-acetylamino)-tetrahydro-pyran-2-ylmethyl ester (172688-22-1)

Guidance literature:

With triethylamine; In dichloromethane; Product distribution; C-silylation depending on the reaction times;

DOI:10.1016/0040-4039(95)01559-0

Reference yield: 75.0%

benzaldehyde (100-52-7) + Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(2-trimethylsilanyl-acetylamino)-tetrahydro-pyran-4-yl ester (172688-21-0) → Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(3-hydroxy-3-phenyl-propionylamino)-tetrahydro-pyran-4-yl ester + Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3)

Guidance literature:

With tetrabutylammonium triphenyldifluorosilicate; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/0040-4039(95)01559-0

Reference yield:

Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(2-trimethylsilanyl-acetylamino)-tetrahydro-pyran-4-yl ester (172688-21-0) → 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / TBAT / tetrahydrofuran / 0 °C

2: 10 percent / Me₃SiOTf, Et₃N / CH₂Cl₂ / 12 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; triethylamine; tetrabutylammonium triphenyldifluorosilicate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(95)01559-0

upstream raw materials:

trimethylsilyl trifluoromethanesulfonate

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

Downstream raw materials:

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

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline