1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose

Base Information

• Chemical Name: 1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose
• CAS No.: 154799-95-8
• Molecular Formula: C₂₁H₂₅NO₁₁
• Molecular Weight: 467.43
• Mol file: 154799-95-8.mol

Synonyms:1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose

Chemical Property of 1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose

There total 40 articles about 1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose 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: 82.0%

(S)-Amino-((2R,3R,4R)-3,4,5-triacetoxy-tetrahydro-furan-2-yl)-acetic acid methyl ester (127559-12-0,127559-14-2) + benzyl chloroformate (501-53-1,94274-21-2) → 1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose (154799-95-8)

Guidance literature:

With sodium hydrogencarbonate; at 0 ℃;

DOI:10.1016/S0040-4039(01)93448-3

Reference yield:

C22H27NO11 → 1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose (154799-95-8)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / acetic acid / 168 h / 5320 Torr

2: 0.168 g / NaHCO₃ / H₂O; dioxane / 0.5 h / 0 °C

With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In 1,4-dioxane; water; acetic acid;

DOI:10.1021/jo9702913

Reference yield:

1,1-Dimethylethyl<2R-<2α(R*),3β,4β>>-2,2-dimethyl-4-(tetrahydro-3,4-dihydroxy-5-oxo-2-furanyl)-3-oxazolidinecarboxylate (127257-26-5) → 1,2,3-Tri-O-acetyl-4-[(S)-Benzyloxycarbonylamino(methoxycarbonyl)methyl]-D-erythrofuranose (154799-95-8)

Guidance literature:

Multi-step reaction with 7 steps

1: DIBAL / toluene / -78 °C

2: Ac₂O / pyridine

3: 77 percent / AcOH / 40 °C

4: NaIO₄ / RuO₄*H₂O / H₂O; acetone

5: diethyl ether / 0 °C

6: 100 percent / TFA / CH₂Cl₂

7: 82 percent / aq. NaHCO₃ / 0 °C

With sodium periodate; acetic anhydride; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; trifluoroacetic acid; ruthenium tetroxide; In pyridine; diethyl ether; dichloromethane; water; acetone; toluene;

DOI:10.1016/S0040-4039(01)93448-3

upstream raw materials:

methanol

(S)-Amino-((2R,3R,4R)-3,4,5-triacetoxy-tetrahydro-furan-2-yl)-acetic acid methyl ester

benzyl chloroformate

diazomethane

Downstream raw materials:

methyl 1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-5-[[(phenylmethoxy)carbonyl]amino]-β-D-allohexofuranuronate 2,3-diacetate

(S)-Benzyloxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid

Methyl 5-amino-1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-allofuranuronate 2,3-diacetate