methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-hydroxypent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate

Base Information

• Chemical Name: methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-hydroxypent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate
• CAS No.: 386765-92-0
• Molecular Formula: C₂₆H₃₁NO₈
• Molecular Weight: 485.534
• Mol file: 386765-92-0.mol

Synonyms:methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-hydroxypent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate

Chemical Property of methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-hydroxypent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-hydroxypent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate

There total 22 articles about methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-hydroxypent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate 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: 86.0%

methyl (E,2S,3R,4R)-4-benzyloxy-3,8-dihydroxy-2-(4-methoxybenzyloxymethyl)-2-(trichloroacetamido)oct-6-enoate (386765-90-8) → methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-hydroxypent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate (386765-92-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 25 ℃; for 20h;

DOI:10.1246/bcsj.75.1927

Reference yield:

methyl (S)-2-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-3-(4-methoxybenzyloxy)-2-(trichloroacetamido)propanoate (386765-87-3) → methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-hydroxypent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate (386765-92-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / aqueous HCl / tetrahydrofuran / 10 h / 25 °C

2: 89 percent / toluene / 20 h / 25 °C

3: 82 percent / DIBAL-H / tetrahydrofuran; toluene / 0.25 h / -18 °C

4: 86 percent / DBU / CH₂Cl₂ / 20 h / 25 °C

With hydrogenchloride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1246/bcsj.75.1927

Reference yield:

methyl (S)-2-[(2R,3R,5RS)-3-benzyloxy-5-hydroxyoxolan-2-yl]-3-(4-methoxybenzyloxy)-2-(trichloroacetamido)propanoate → methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-hydroxypent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate (386765-92-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / toluene / 20 h / 25 °C

2: 82 percent / DIBAL-H / tetrahydrofuran; toluene / 0.25 h / -18 °C

3: 86 percent / DBU / CH₂Cl₂ / 20 h / 25 °C

With diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1246/bcsj.75.1927

upstream raw materials:

methyl (E,2S,3R,4R)-4-benzyloxy-3,8-dihydroxy-2-(4-methoxybenzyloxymethyl)-2-(trichloroacetamido)oct-6-enoate

(D)-mannose diacetonide

2,3,5,6-di-O-isopropylidene-D-mannofuranose

1,4-anhydro-2-deoxy-5,6-O-isopropylidene-D-arabinohex-1-enitol

Downstream raw materials:

(4S,5R)-5-[(E)-(R)-6-Benzenesulfonyl-1-benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

(4S,5R)-5-[(E)-(R)-6-Benzenesulfonyl-1-benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid

methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-bromopent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate

(4S,5R)-5-((E)-(R)-1-Benzyloxy-5-methanesulfonyloxy-pent-3-enyl)-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester