1,2,3-Tri-O-acetyl-4-[(1R,4R,2E)-4-acetoxy-1-benzyloxycarbonylaminopent-2-enyl]-D-erythrofuranose

Base Information

• Chemical Name: 1,2,3-Tri-O-acetyl-4-[(1R,4R,2E)-4-acetoxy-1-benzyloxycarbonylaminopent-2-enyl]-D-erythrofuranose
• CAS No.: 154674-75-6
• Molecular Formula: C₂₅H₃₁NO₁₁
• Molecular Weight: 521.521

Synonyms:1,2,3-Tri-O-acetyl-4-[(1R,4R,2E)-4-acetoxy-1-benzyloxycarbonylaminopent-2-enyl]-D-erythrofuranose

Chemical Property of 1,2,3-Tri-O-acetyl-4-[(1R,4R,2E)-4-acetoxy-1-benzyloxycarbonylaminopent-2-enyl]-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-[(1R,4R,2E)-4-acetoxy-1-benzyloxycarbonylaminopent-2-enyl]-D-erythrofuranose

There total 15 articles about 1,2,3-Tri-O-acetyl-4-[(1R,4R,2E)-4-acetoxy-1-benzyloxycarbonylaminopent-2-enyl]-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:

3-O-(4-Methoxybenzyl)-4-[(R,E)-4-benzyloxymethoxy-3-oxopent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose (154674-70-1) → 1,2,3-Tri-O-acetyl-4-[(1R,4R,2E)-4-acetoxy-1-benzyloxycarbonylaminopent-2-enyl]-D-erythrofuranose (154674-75-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 98 percent / Zn(BH₄)2 / diethyl ether / 6 h / -40 °C

2.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -78 °C

2.2: 98 percent / tetrahydrofuran / 1 h / -78 °C

3.1: 98 percent / xylene / 12 h / Heating

4.1: 100 percent / Ba(OH)2; MeOH / 16 h / 0 °C

5.1: 96 percent / KHCO₃; H₂O / ethyl acetate / 14 h / 20 °C

6.1: 73 percent / DDQ; H₂O / CH₂Cl₂; 2-methyl-propan-2-ol / pH 7

7.1: 98 percent / NEt₃; DMAP / CH₂Cl₂ / 1 h / 20 °C

8.1: AcOH; H₂O / 40 h / 70 °C

9.1: NEt₃; DMAP / CH₂Cl₂ / 0.75 h / 20 °C

With methanol; dmap; barium dihydroxide; n-butyllithium; zinc(II) tetrahydroborate; water; potassium hydrogencarbonate; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; xylene; tert-butyl alcohol; 1.1: Reduction / 2.1: Metallation / 2.2: Addition / 3.1: Rearrangement / 4.1: Deacylation / 5.1: Acylation / 6.1: Oxidation / 7.1: Acetylation / 8.1: Hydrolysis / 9.1: Acetylation;

DOI:10.1039/a905771d

Reference yield:

acetic anhydride (108-24-7) + Acetic acid (2R,3S,4R)-2-((E)-(1R,4R)-1-benzyloxycarbonylamino-4-hydroxy-pent-2-enyl)-4,5-dihydroxy-tetrahydro-furan-3-yl ester → 1,2,3-Tri-O-acetyl-4-[(1R,4R,2E)-4-acetoxy-1-benzyloxycarbonylaminopent-2-enyl]-D-erythrofuranose (154674-75-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1039/a905771d

Reference yield:

3-O-(4-Methoxybenzyl)-4-[(3S,4R,1E)-4-benzyloxymethoxy-3-hydroxypent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose (154674-71-2) → 1,2,3-Tri-O-acetyl-4-[(1R,4R,2E)-4-acetoxy-1-benzyloxycarbonylaminopent-2-enyl]-D-erythrofuranose (154674-75-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -78 °C

1.2: 98 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 98 percent / xylene / 12 h / Heating

3.1: 100 percent / Ba(OH)2; MeOH / 16 h / 0 °C

4.1: 96 percent / KHCO₃; H₂O / ethyl acetate / 14 h / 20 °C

5.1: 73 percent / DDQ; H₂O / CH₂Cl₂; 2-methyl-propan-2-ol / pH 7

6.1: 98 percent / NEt₃; DMAP / CH₂Cl₂ / 1 h / 20 °C

7.1: AcOH; H₂O / 40 h / 70 °C

8.1: NEt₃; DMAP / CH₂Cl₂ / 0.75 h / 20 °C

With methanol; dmap; barium dihydroxide; n-butyllithium; water; potassium hydrogencarbonate; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; xylene; tert-butyl alcohol; 1.1: Metallation / 1.2: Addition / 2.1: Rearrangement / 3.1: Deacylation / 4.1: Acylation / 5.1: Oxidation / 6.1: Acetylation / 7.1: Hydrolysis / 8.1: Acetylation;

DOI:10.1039/a905771d

upstream raw materials:

acetic anhydride

3-O-(4-Methoxybenzyl)-4-[(1R,4R,2E)-4-benzyloxycarbonylamino-4-benzyloxymethoxypent-2-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose

(R)-1-[(3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol

3-O-(4-Methoxybenzyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Downstream raw materials:

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

(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 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

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