[(2S,3R,4S)-3-acetyloxy-2-methyl-3,4-dihydro-2H-pyran-4-yl] acetate

Base Information

• Chemical Name: [(2S,3R,4S)-3-acetyloxy-2-methyl-3,4-dihydro-2H-pyran-4-yl] acetate
• CAS No.: 54621-94-2
• Molecular Formula: C10H14 O5
• Molecular Weight: 214.218
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID80350797
• Nikkaji Number: J1.408.876H,J647.058K
• Wikidata: Q82126901
• Mol file: 54621-94-2.mol

Synonyms:3,4-DI-O-ACETYL-L-FUCAL;54621-94-2;91926-31-7;3,4-DI-O-ACETYL-2,6-ANHYDRO-1,5-DIDEOXY-L-ARABINO-HEX-5-ENITOL;[(2S,3R,4S)-3-acetyloxy-2-methyl-3,4-dihydro-2H-pyran-4-yl] acetate;(2S,3R,4S)-2-Methyl-3,4-dihydro-2H-pyran-3,4-diyl diacetate;AC1LELE9;SCHEMBL2614789;DTXSID80350797;NDEGMKQAZZBNBB-JMOVZRAMSA-N;MFCD06799015;VT1004;HY-24463;MS-23171;PD130998;CS-0254423;F83258;A917033;(2S,3R,4S)-2-Methyl-3,4-dihydro-2H-pyran-3,4-diyldiacetate;L-arabino-Hex-5-enitol, 2,6-anhydro-1,5-dideoxy-, 3,4-diacetate

Chemical Property of [(2S,3R,4S)-3-acetyloxy-2-methyl-3,4-dihydro-2H-pyran-4-yl] acetate

Chemical Property:

• Vapor Pressure: 0.00149mmHg at 25°C
• Boiling Point: 295.9°Cat760mmHg
• Flash Point: 116.5°C
• PSA: 61.83000
• Density: 1.16g/cm³
• LogP: 0.78220
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 214.08412354
• Heavy Atom Count: 15
• Complexity: 284

Purity/Quality:

98% ^*data from raw suppliers

3,4-Di-O-acetyl-L-fucal ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C=CO1)OC(=O)C)OC(=O)C
• Isomeric SMILES: C[C@H]1[C@H]([C@H](C=CO1)OC(=O)C)OC(=O)C
• Uses: 3,4-di-O-acetyl-2,6-anhydro-1,5-dideoxy-L-arabino-hex-5-enitol is an intermediate used in the synthesis of 2,6-Dideoxy-2-fluoro-L-galactopyranose 1,3,4-Triacetate (D440910), which is a reactant in the preparation of β-purine-diphosphate sugars (GDP-fucose-analogs)

Technology Process of [(2S,3R,4S)-3-acetyloxy-2-methyl-3,4-dihydro-2H-pyran-4-yl] acetate

There total 2 articles about [(2S,3R,4S)-3-acetyloxy-2-methyl-3,4-dihydro-2H-pyran-4-yl] acetate 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:

2-methyl-2,3-dihydro-4H-pyran-4-one (19185-89-8,190912-15-3) → Acetic acid (2S,4S)-4-acetoxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester (34819-86-8,54621-94-2,69483-67-6,75829-69-5,76739-66-7,80483-15-4,81844-95-3,87335-76-0,91926-31-7,115888-74-9,125589-90-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Mn(OAc)3 / benzene / 24 h / Heating

2: 1.) NaBH₄ / 1.) CeCl₃ 2.) Et₃N

With sodium tetrahydroborate; manganese triacetate; In benzene;

DOI:10.1016/S0040-4039(00)98650-7

Reference yield:

acetic anhydride (108-24-7) + Acetic acid 2-methyl-4-oxo-3,4-dihydro-2H-pyran-3-yl ester (68673-59-6,80483-18-7,102131-06-6,102131-07-7,143396-42-3) → Acetic acid (2S,4S)-4-acetoxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester (34819-86-8,54621-94-2,69483-67-6,75829-69-5,76739-66-7,80483-15-4,81844-95-3,87335-76-0,91926-31-7,115888-74-9,125589-90-4)

Guidance literature:

With sodium tetrahydroborate; Yield given. Multistep reaction; 1.) CeCl₃ 2.) Et₃N;

DOI:10.1016/S0040-4039(00)98650-7

Reference yield: 90.0%

3,4-di-O-acetyl-L-fucal (54621-94-2) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranoside (128135-62-6)

Guidance literature:

With 4 A molecular sieve; trimsyl triflate; triethylamine; In dichloromethane; at -65 ℃; for 2h;

DOI:10.1016/0008-6215(90)80090-P

upstream raw materials:

acetic anhydride

Acetic acid 2-methyl-4-oxo-3,4-dihydro-2H-pyran-3-yl ester

2-methyl-2,3-dihydro-4H-pyran-4-one

Downstream raw materials:

L-fucal

7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-talopyranosyl)daunomycinone

benzyl 2,3,6-trideoxy-4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-3-trifluoroacetamido-α-L-lyxo-hexopyranoside

benzyl 4)-O-(3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-(1->4)-(2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside)>

Refernces