5'-O-benzyl-2'-deoxy-3-N-(p-methoxybenzyl)-3'-oxohydantocidin

Base Information

• Chemical Name: 5'-O-benzyl-2'-deoxy-3-N-(p-methoxybenzyl)-3'-oxohydantocidin
• CAS No.: 130607-49-7
• Molecular Formula: C₂₂H₂₂N₂O₆
• Molecular Weight: 410.426
• Mol file: 130607-49-7.mol

Synonyms:5'-O-benzyl-2'-deoxy-3-N-(p-methoxybenzyl)-3'-oxohydantocidin

Chemical Property of 5'-O-benzyl-2'-deoxy-3-N-(p-methoxybenzyl)-3'-oxohydantocidin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-benzyl-2'-deoxy-3-N-(p-methoxybenzyl)-3'-oxohydantocidin

There total 8 articles about 5'-O-benzyl-2'-deoxy-3-N-(p-methoxybenzyl)-3'-oxohydantocidin 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: 55.0%

(2'R,3'R,5Z)-5-(4'-benzyloxy-2',3'-dihydroxybutylidene)-3-(p-methoxybenzyl)hydantoin (141782-37-8) → (5R,7R)-7-Benzyloxymethyl-3-(4-methoxy-benzyl)-6-oxa-1,3-diaza-spiro[4.4]nonane-2,4,8-trione (130508-79-1) + 5'-O-benzyl-2'-deoxy-3-N-(p-methoxybenzyl)-3'-oxohydantocidin (130607-49-7)

Guidance literature:

(2'R,3'R,5Z)-5-(4'-benzyloxy-2',3'-dihydroxybutylidene)-3-(p-methoxybenzyl)hydantoin; With triethylamine; In 1,2-dichloro-ethane; for 6h; Heating;

With 3 A molecular sieve; sodium acetate; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 0.25h; Further stages.;

DOI:10.1002/(SICI)1099-0690(200005)2000:9<1831::AID-EJOC1831>3.0.CO;2-S

Reference yield:

N-acetyl N-methoxybenzylhydantoin (129744-26-9) → 5'-O-benzyl-2'-deoxy-3-N-(p-methoxybenzyl)-3'-oxohydantocidin (130607-49-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 89 percent / tBuOK / tetrahydrofuran / 0 - 20 °C

2.1: 75 percent / ethylene glycol; methanol; TsOH*H₂O / CH₂Cl₂ / 48 h / 20 °C

3.1: Et₃N / 1,2-dichloro-ethane / 6 h / Heating

3.2: 55 percent / molecular sieves 3 Angstroem; PCC; NaOAc / CH₂Cl₂ / 0.25 h / 20 °C

With methanol; potassium tert-butylate; toluene-4-sulfonic acid; ethylene glycol; triethylamine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; 1.1: Condensation / 2.1: Decomposition / 3.1: Cyclization / 3.2: Oxidation;

DOI:10.1002/(SICI)1099-0690(200005)2000:9<1831::AID-EJOC1831>3.0.CO;2-S

Reference yield:

4-O-benzyl-2,3-O-isopropylidene-D-threose (81801-09-4) → 5'-O-benzyl-2'-deoxy-3-N-(p-methoxybenzyl)-3'-oxohydantocidin (130607-49-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 89 percent / tBuOK / tetrahydrofuran / 0 - 20 °C

2.1: 75 percent / ethylene glycol; methanol; TsOH*H₂O / CH₂Cl₂ / 48 h / 20 °C

3.1: Et₃N / 1,2-dichloro-ethane / 6 h / Heating

3.2: 55 percent / molecular sieves 3 Angstroem; PCC; NaOAc / CH₂Cl₂ / 0.25 h / 20 °C

With methanol; potassium tert-butylate; toluene-4-sulfonic acid; ethylene glycol; triethylamine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; 1.1: Condensation / 2.1: Decomposition / 3.1: Cyclization / 3.2: Oxidation;

DOI:10.1002/(SICI)1099-0690(200005)2000:9<1831::AID-EJOC1831>3.0.CO;2-S

upstream raw materials:

(2'R,3'R,5Z)-5-(4'-benzyloxy-2',3'-dihydroxybutylidene)-3-(p-methoxybenzyl)hydantoin

4-O-benzyl-2,3-O-isopropylidene-D-threose

N-acetyl N-methoxybenzylhydantoin

5-Z-<(2R,3R)-4-benzyloxy-2,3-isopropylidenedioxy>butylidene-3-(4-methoxybenzyl)hydantoin

Downstream raw materials:

5'-O-benzyl-2'-deoxy-3-N-(p-methoxybenzyl)hydantocidin

5'-O-benzyl-2'-deoxyhydantocidin