1-O-benzyl-5-O-[1-(4-benzyloxycarbonylbutyl)]-phosphono-L-erythro-pent-2-ulose

Base Information

• Chemical Name: 1-O-benzyl-5-O-[1-(4-benzyloxycarbonylbutyl)]-phosphono-L-erythro-pent-2-ulose
• CAS No.: 216770-64-8
• Molecular Formula: C₂₄H₃₁O₁₀P
• Molecular Weight: 510.478
• Mol file: 216770-64-8.mol

Synonyms:1-O-benzyl-5-O-[1-(4-benzyloxycarbonylbutyl)]-phosphono-L-erythro-pent-2-ulose

Chemical Property of 1-O-benzyl-5-O-[1-(4-benzyloxycarbonylbutyl)]-phosphono-L-erythro-pent-2-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-benzyl-5-O-[1-(4-benzyloxycarbonylbutyl)]-phosphono-L-erythro-pent-2-ulose

There total 7 articles about 1-O-benzyl-5-O-[1-(4-benzyloxycarbonylbutyl)]-phosphono-L-erythro-pent-2-ulose 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: 35.0%

1-O-benzyl-5-O-[1-(4-benzyloxycarbonylbutyl)]-phosphono-L-erythro-pent-2-ulose ethane-1,2-diyl dithioacetal (216770-60-4) → 1-O-benzyl-5-O-[1-(4-benzyloxycarbonylbutyl)]-phosphono-L-erythro-pent-2-ulose (216770-64-8)

Guidance literature:

With methyl iodide; In phosphate buffer; acetonitrile; at 50 ℃; for 7h; pH=7.6;

DOI:10.1080/07328309808001895

Reference yield:

5-hydroxypentanoic acid sodium salt (37435-69-1) → 1-O-benzyl-5-O-[1-(4-benzyloxycarbonylbutyl)]-phosphono-L-erythro-pent-2-ulose (216770-64-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 40 percent / dimethylformamide

2.1: triethylamine / CH₂Cl₂ / 2 h / 20 °C

2.2: 48 percent / triethylamine / CH₂Cl₂ / 6 h / 20 °C

3.1: 63 percent / Na₂CO₃ / H₂O; acetonitrile / 1 h / 20 °C

4.1: 35 percent / CH₃I / acetonitrile; aq. phosphate buffer / 7 h / 50 °C / pH 7.6

With sodium carbonate; triethylamine; methyl iodide; In phosphate buffer; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Substitution / 2.1: Esterification / 2.2: Substitution / 3.1: Hydrolysis / 4.1: Decomposition;

DOI:10.1080/07328309808001895

Reference yield:

(3S,4S)-2-Benzyloxymethyl-tetrahydro-furan-2,3,4-triol (130114-53-3,130114-54-4) → 1-O-benzyl-5-O-[1-(4-benzyloxycarbonylbutyl)]-phosphono-L-erythro-pent-2-ulose (216770-64-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 75 percent / HCl / H₂O / 0.5 h / 0 °C

2.1: triethylamine / CH₂Cl₂ / 2 h / 20 °C

2.2: 48 percent / triethylamine / CH₂Cl₂ / 6 h / 20 °C

3.1: 63 percent / Na₂CO₃ / H₂O; acetonitrile / 1 h / 20 °C

4.1: 35 percent / CH₃I / acetonitrile; aq. phosphate buffer / 7 h / 50 °C / pH 7.6

With hydrogenchloride; sodium carbonate; triethylamine; methyl iodide; In phosphate buffer; dichloromethane; water; acetonitrile; 1.1: thioketalisation / 2.1: Esterification / 2.2: Substitution / 3.1: Hydrolysis / 4.1: Decomposition;

DOI:10.1080/07328309808001895

upstream raw materials:

1-O-benzyl-5-O-[1-(4-benzyloxycarbonylbutyl)]-phosphono-L-erythro-pent-2-ulose ethane-1,2-diyl dithioacetal

(3S,4S)-2-Benzyloxymethyl-tetrahydro-furan-2,3,4-triol

5-hydroxypentanoic acid sodium salt

benzyl chloride