3,4-di-O-acetyl-D-rhamnal

Base Information

• Chemical Name: 3,4-di-O-acetyl-D-rhamnal
• CAS No.: 76739-66-7
• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.218
• Mol file: 76739-66-7.mol

Synonyms:3,4-di-O-acetyl-D-rhamnal

Chemical Property of 3,4-di-O-acetyl-D-rhamnal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-di-O-acetyl-D-rhamnal

There total 2 articles about 3,4-di-O-acetyl-D-rhamnal 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: 83.0%

benzyl bromide (100-39-0) + 3,4-di-O-acetyl-D-rhamnal (76739-66-7) → 1,5-anhydro-3,4-di-O-benzyl-2,6-dideoxy-D-arabino-hex-1-enitol (111002-90-5)

Guidance literature:

3,4-di-O-acetyl-D-rhamnal; With sodium methylate; In methanol; at 0 ℃; for 3h;

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil;

DOI:10.1055/s-0037-1611916

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:

benzyl 4-O-acetyl-6-deoxy-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside

benzyl 3,4-di-O-acetyl-2-bromo-2,6-dideoxy-α-D-mannopyranoside

3,4-di-O-acetyl-1,2-dideoxy-1,2-di-(p-toluenesulfonamido)-β-D-rhamnopyranose

methyl 3-O-benzyl-4-O-(3-O-benzyl-4-O-benzylsulfonyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside

Refernces