(Z)-2-[((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-but-2-enedioic acid 1-ethyl ester 4-methyl ester

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Chemical Name:(Z)-2-[((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-but-2-enedioic acid 1-ethyl ester 4-methyl ester
CAS No.:182156-05-4
Molecular Formula:C₂₁H₂₈O₈
Molecular Weight:408.449
Hs Code.:

Synonyms:(Z)-2-[((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-but-2-enedioic acid 1-ethyl ester 4-methyl ester

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Chemical Property of (Z)-2-[((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-but-2-enedioic acid 1-ethyl ester 4-methyl ester

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Technology Process of (Z)-2-[((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-but-2-enedioic acid 1-ethyl ester 4-methyl ester

There total 6 articles about (Z)-2-[((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-but-2-enedioic acid 1-ethyl ester 4-methyl 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: 96.0%

: 182156-04-3
(4'R,5'S)-5'-Benzyloxymethyl-5-methoxycarbonylmethyl-2',2'-dimethyl-2-oxo-[4,4']bi[[1,3]dioxolanyl]-5-carboxylic acid ethyl ester

: 182156-05-4
(Z)-2-[((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-but-2-enedioic acid 1-ethyl ester 4-methyl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/jo960963+

Reference yield:

: 65434-72-2
2-(triphenylphosphoranylidene)succinic acid 1-ethyl ester

: 182156-05-4
(Z)-2-[((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-but-2-enedioic acid 1-ethyl ester 4-methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / benzene / 24 h / 25 °C

2: 96 percent / Et₃N / various solvent(s) / 48 h / Ambient temperature

3: 89 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / 168 h / Ambient temperature

4: 91 percent / benzene / 5 h / Ambient temperature

5: 96 percent / DBU / tetrahydrofuran / 1 h / 0 °C

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; water; acetone; benzene;
DOI:10.1021/jo960963+

Reference yield:

: 81028-12-8
(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

: 182156-05-4
(Z)-2-[((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-but-2-enedioic acid 1-ethyl ester 4-methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / benzene / 24 h / 25 °C

2: 96 percent / Et₃N / various solvent(s) / 48 h / Ambient temperature

3: 89 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / 168 h / Ambient temperature

4: 91 percent / benzene / 5 h / Ambient temperature

5: 96 percent / DBU / tetrahydrofuran / 1 h / 0 °C

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; water; acetone; benzene;
DOI:10.1021/jo960963+