Acetic acid (2S,5R,6R)-6-bromo-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2S,5R,6R)-6-bromo-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 113886-85-4
• Molecular Formula: C₁₄H₁₆BrN₃O₇
• Molecular Weight: 418.201
• Mol file: 113886-85-4.mol

Synonyms:Acetic acid (2S,5R,6R)-6-bromo-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Acetic acid (2S,5R,6R)-6-bromo-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,5R,6R)-6-bromo-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ylmethyl ester

There total 1 articles about Acetic acid (2S,5R,6R)-6-bromo-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ylmethyl 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 anhydride (108-24-7) + (3R,6S)-3-(2,4-Dinitro-phenylamino)-6-hydroxymethyl-tetrahydro-pyran-2-ol → Acetic acid (2S,5R,6R)-6-bromo-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ylmethyl ester (113886-85-4)

Guidance literature:

With pyridine; hydrogen bromide; acetic acid; Yield given. Multistep reaction; 2.) CHCl₃, 5 deg C, 5 min;

DOI:10.1248/cpb.35.2136

Reference yield: 68.0%

Acetic acid (2S,5R,6R)-6-bromo-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ylmethyl ester (113886-85-4) + methyl 4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside (60076-41-7) → Acetic acid (2S,5R,6R)-6-((4aR,6S,7R,8R,8aS)-7-benzyloxycarbonylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ylmethyl ester (113886-86-5)

Guidance literature:

With 2,4,6-trimethyl-pyridine; silver perchlorate; In 1,4-dioxane; benzene; at 27 ℃; for 0.25h;

DOI:10.1248/cpb.35.2136

Reference yield:

Acetic acid (2S,5R,6R)-6-bromo-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ylmethyl ester (113886-85-4) → [(4aR,6S,7R,8R,8aS)-8-((2R,3R,6S)-6-Azidomethyl-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / AgClO₄, sym-collidine / benzene; dioxane / 0.25 h / 27 °C

2: Dowex 1*2(OH₁-) / acetone; H₂O / 25 °C

3: NaHCO₃ / dioxane; H₂O / 2 °C

4: pyridine

5: NaN₃ / dimethylformamide / 80 °C

With pyridine; 2,4,6-trimethyl-pyridine; sodium azide; Dowex 1*2(OH₁-); silver perchlorate; sodium hydrogencarbonate; In 1,4-dioxane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1248/cpb.35.2136

upstream raw materials:

acetic anhydride

Downstream raw materials:

Acetic acid (2S,5R,6R)-6-((4aR,6S,7R,8R,8aS)-7-benzyloxycarbonylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-5-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ylmethyl ester

[(4aR,6S,7R,8R,8aS)-8-((2R,3R,6S)-3-Benzyloxycarbonylamino-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester

Acetic acid (3S,4R,5R,6S)-2-acetoxy-4-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yl ester

{(4aR,6S,7R,8R,8aS)-8-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-carbamic acid benzyl ester