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

Base Information

• Chemical Name: 4-[(1R,4R,2E)-4-Benzyloxycarbonylamino-4-benzyloxymethoxypent-2-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose
• CAS No.: 261171-78-2
• Molecular Formula: C₂₈H₃₅NO₈
• Molecular Weight: 513.588

Synonyms:4-[(1R,4R,2E)-4-Benzyloxycarbonylamino-4-benzyloxymethoxypent-2-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose

Chemical Property of 4-[(1R,4R,2E)-4-Benzyloxycarbonylamino-4-benzyloxymethoxypent-2-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose

Chemical Property:

Purity/Quality:

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Technology Process of 4-[(1R,4R,2E)-4-Benzyloxycarbonylamino-4-benzyloxymethoxypent-2-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose

There total 11 articles about 4-[(1R,4R,2E)-4-Benzyloxycarbonylamino-4-benzyloxymethoxypent-2-enyl]-1,2-O-isopropylidene-α-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: 73.0%

3-O-(4-Methoxybenzyl)-4-[(1R,4R,2E)-4-benzyloxycarbonylamino-4-benzyloxymethoxypent-2-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose (154674-74-5) → 4-[(1R,4R,2E)-4-Benzyloxycarbonylamino-4-benzyloxymethoxypent-2-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose (261171-78-2)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; tert-butyl alcohol; pH=7;

DOI:10.1039/a905771d

Reference yield:

Dimethyl [(3R)-3-benzyloxymethoxy-2-oxobutyl]phosphonate (96823-34-6) → 4-[(1R,4R,2E)-4-Benzyloxycarbonylamino-4-benzyloxymethoxypent-2-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose (261171-78-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 94 percent / LiCl; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 20 °C

2.1: 98 percent / Zn(BH₄)2 / diethyl ether / 6 h / -40 °C

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

3.2: 98 percent / tetrahydrofuran / 1 h / -78 °C

4.1: 98 percent / xylene / 12 h / Heating

5.1: 100 percent / Ba(OH)2; MeOH / 16 h / 0 °C

6.1: 96 percent / KHCO₃; H₂O / ethyl acetate / 14 h / 20 °C

7.1: 73 percent / DDQ; H₂O / CH₂Cl₂; 2-methyl-propan-2-ol / pH 7

With methanol; barium dihydroxide; n-butyllithium; zinc(II) tetrahydroborate; water; potassium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; acetonitrile; xylene; tert-butyl alcohol; 1.1: Condensation / 2.1: Reduction / 3.1: Metallation / 3.2: Addition / 4.1: Rearrangement / 5.1: Deacylation / 6.1: Acylation / 7.1: Oxidation;

DOI:10.1039/a905771d

Reference yield:

(R)-1-[(3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol (69940-04-1,142226-16-2,109536-51-8) → 4-[(1R,4R,2E)-4-Benzyloxycarbonylamino-4-benzyloxymethoxypent-2-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose (261171-78-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 96 percent / lead tetraacetate; Na₂CO₃ / CH₂Cl₂ / 2 h / 0 °C

2.1: 94 percent / LiCl; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 20 °C

3.1: 98 percent / Zn(BH₄)2 / diethyl ether / 6 h / -40 °C

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

4.2: 98 percent / tetrahydrofuran / 1 h / -78 °C

5.1: 98 percent / xylene / 12 h / Heating

6.1: 100 percent / Ba(OH)2; MeOH / 16 h / 0 °C

7.1: 96 percent / KHCO₃; H₂O / ethyl acetate / 14 h / 20 °C

8.1: 73 percent / DDQ; H₂O / CH₂Cl₂; 2-methyl-propan-2-ol / pH 7

With lead(IV) acetate; methanol; barium dihydroxide; n-butyllithium; zinc(II) tetrahydroborate; water; sodium carbonate; potassium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; acetonitrile; xylene; tert-butyl alcohol; 1.1: Oxidation / 2.1: Condensation / 3.1: Reduction / 4.1: Metallation / 4.2: Addition / 5.1: Rearrangement / 6.1: Deacylation / 7.1: Acylation / 8.1: Oxidation;

DOI:10.1039/a905771d

upstream raw materials:

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

Dimethyl [(3R)-3-benzyloxymethoxy-2-oxobutyl]phosphonate

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

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

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

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