(E)-(R)-4-{(4S,5R)-5-[(E)-(S)-1-Benzyloxy-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-(4-methoxy-benzyloxy)-but-2-enoic acid ethyl ester

Base Information

Chemical Name:(E)-(R)-4-{(4S,5R)-5-[(E)-(S)-1-Benzyloxy-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-(4-methoxy-benzyloxy)-but-2-enoic acid ethyl ester
CAS No.:182411-41-2
Molecular Formula:C₃₅H₄₆O₉
Molecular Weight:610.745
Hs Code.:

(E)-(R)-4-{(4S,5R)-5-[(E)-(S)-1-Benzyloxy-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-(4-methoxy-benzyloxy)-but-2-enoic acid ethyl ester

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Chemical Property of (E)-(R)-4-{(4S,5R)-5-[(E)-(S)-1-Benzyloxy-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-(4-methoxy-benzyloxy)-but-2-enoic acid ethyl ester

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Technology Process of (E)-(R)-4-{(4S,5R)-5-[(E)-(S)-1-Benzyloxy-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-(4-methoxy-benzyloxy)-but-2-enoic acid ethyl ester

There total 9 articles about (E)-(R)-4-{(4S,5R)-5-[(E)-(S)-1-Benzyloxy-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-(4-methoxy-benzyloxy)-but-2-enoic acid ethyl ester 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:

: 110-87-2
3,4-dihydro-2H-pyran

: 182411-41-2
(E)-(R)-4-{(4S,5R)-5-[(E)-(S)-1-Benzyloxy-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-(4-methoxy-benzyloxy)-but-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

2: 100 percent / TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

3: (COCl)2, DMSO / CH₂Cl₂ / 1 h / -78 °C

4: 1.) t-BuOK / 1.) THF, 0 deg C, 1.5 h, 2.) THF, -78 deg C, 30 min

With oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0040-4020(96)00700-4

Reference yield:

: 100-39-0
benzyl bromide

: 182411-41-2
(E)-(R)-4-{(4S,5R)-5-[(E)-(S)-1-Benzyloxy-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-(4-methoxy-benzyloxy)-but-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 97 percent / NaH / tetrahydrofuran / 15 h / Ambient temperature

2: 1.) (PPh₃)3RhCl, (i-Pr)2NEt, 2.) HgO, HgCl₂ / 1.) EtOH, reflux, 3 h, 2.) acetone, water, RT, 30 min

3: 67 percent / benzene / 6 h / Heating

4: 69 percent / TfOH / diethyl ether / Ambient temperature

5: 1.) DIBAL, 2.) NaBH₄, CeCl₃ / 1.) dichloromethane, hexane, -78 deg C, 30 min, 2.) MeOH, RT

6: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

7: 100 percent / TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

8: (COCl)2, DMSO / CH₂Cl₂ / 1 h / -78 °C

9: 1.) t-BuOK / 1.) THF, 0 deg C, 1.5 h, 2.) THF, -78 deg C, 30 min

With sodium tetrahydroborate; Wilkinson's catalyst; cerium(III) chloride; oxalyl dichloride; trifluorormethanesulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1016/0040-4020(96)00700-4

Reference yield:

: 182411-29-6
(3aS,4R,6S,7R,7aR)-6-Allyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

: 182411-41-2
(E)-(R)-4-{(4S,5R)-5-[(E)-(S)-1-Benzyloxy-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-(4-methoxy-benzyloxy)-but-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 97 percent / NaH / tetrahydrofuran / 15 h / Ambient temperature

2: 1.) (PPh₃)3RhCl, (i-Pr)2NEt, 2.) HgO, HgCl₂ / 1.) EtOH, reflux, 3 h, 2.) acetone, water, RT, 30 min

3: 67 percent / benzene / 6 h / Heating

4: 69 percent / TfOH / diethyl ether / Ambient temperature

5: 1.) DIBAL, 2.) NaBH₄, CeCl₃ / 1.) dichloromethane, hexane, -78 deg C, 30 min, 2.) MeOH, RT

6: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

7: 100 percent / TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

8: (COCl)2, DMSO / CH₂Cl₂ / 1 h / -78 °C

9: 1.) t-BuOK / 1.) THF, 0 deg C, 1.5 h, 2.) THF, -78 deg C, 30 min

With sodium tetrahydroborate; Wilkinson's catalyst; cerium(III) chloride; oxalyl dichloride; trifluorormethanesulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1016/0040-4020(96)00700-4