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

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Chemical Name:3-O-(4-Methoxybenzyl)-4-[(1R,4R,2E)-4-benzyloxycarbonylamino-4-benzyloxymethoxypent-2-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose
CAS No.:154674-74-5
Molecular Formula:C₃₆H₄₃NO₉
Molecular Weight:633.739
Hs Code.:

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

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

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

There total 14 articles about 3-O-(4-Methoxybenzyl)-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: 96.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 261171-77-1
(E)-(1R,4R)-4-Benzyloxymethoxy-1-[(3aR,5R,6R,6aR)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-pent-2-enylamine

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

Guidance literature:: With water; potassium hydrogencarbonate; In ethyl acetate; at 20 ℃; for 14h;
DOI:10.1039/a905771d

Reference yield:

: 96823-34-6
Dimethyl [(3R)-3-benzyloxymethoxy-2-oxobutyl]phosphonate

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

Guidance literature:: Multi-step reaction with 6 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

With methanol; barium dihydroxide; n-butyllithium; zinc(II) tetrahydroborate; water; potassium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; diethyl ether; hexane; ethyl acetate; acetonitrile; xylene; 1.1: Condensation / 2.1: Reduction / 3.1: Metallation / 3.2: Addition / 4.1: Rearrangement / 5.1: Deacylation / 6.1: Acylation;
DOI:10.1039/a905771d

Reference yield:

: 154674-70-1
3-O-(4-Methoxybenzyl)-4-[(R,E)-4-benzyloxymethoxy-3-oxopent-1-enyl]-1,2-O-isopropylidene-α-D-erythrofuranose

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

Guidance literature:: Multi-step reaction with 5 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

With methanol; barium dihydroxide; n-butyllithium; zinc(II) tetrahydroborate; water; potassium hydrogencarbonate; In tetrahydrofuran; diethyl ether; hexane; ethyl acetate; xylene; 1.1: Reduction / 2.1: Metallation / 2.2: Addition / 3.1: Rearrangement / 4.1: Deacylation / 5.1: Acylation;
DOI:10.1039/a905771d