Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 287973-47-1
• Molecular Formula: C₂₂H₂₃F₃N₂O₁₀
• Molecular Weight: 532.427
• Mol file: 287973-47-1.mol

Synonyms:Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3-yl ester

There total 1 articles about Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-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: 43.0%

3-(4-hydroxyphenyl)-3-trifluoromethyldiazirine (156824-51-0) + β-D-galactose peracetate (4163-60-4) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3-yl ester (287973-47-1)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/S0960-894X(00)00180-3

Reference yield: 90.0%

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3-yl ester (287973-47-1) → (2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3,4,5-triol (287973-40-4)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 5h;

DOI:10.1016/S0960-894X(00)00180-3

Reference yield:

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3-yl ester (287973-47-1) → (2S,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-2-carbaldehyde

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / CH₃ONa; CH₃OH / 5 h / 20 °C

2: galactose oxidase; catalase; phosphate buffer / 1 h / 20 °C / pH 7

With methanol; galactose oxidase; phosphate buffer; sodium methylate; catalase; 1: Deacetylation / 2: Oxidation;

DOI:10.1016/S0960-894X(00)00180-3

upstream raw materials:

3-(4-hydroxyphenyl)-3-trifluoromethyldiazirine

β-D-galactose peracetate

Downstream raw materials:

(2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[4-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-tetrahydro-pyran-3,4,5-triol