1-ethyl 6-methyl (E)-4,5-di-O-benzyl-2,3-dideoxy-L-threo-hex-2-enarate

Base Information

Chemical Name:1-ethyl 6-methyl (E)-4,5-di-O-benzyl-2,3-dideoxy-L-threo-hex-2-enarate
CAS No.:853799-31-2
Molecular Formula:C₂₃H₂₆O₆
Molecular Weight:398.456
Hs Code.:

Synonyms:1-ethyl 6-methyl (E)-4,5-di-O-benzyl-2,3-dideoxy-L-threo-hex-2-enarate

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Chemical Property of 1-ethyl 6-methyl (E)-4,5-di-O-benzyl-2,3-dideoxy-L-threo-hex-2-enarate

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Technology Process of 1-ethyl 6-methyl (E)-4,5-di-O-benzyl-2,3-dideoxy-L-threo-hex-2-enarate

There total 4 articles about 1-ethyl 6-methyl (E)-4,5-di-O-benzyl-2,3-dideoxy-L-threo-hex-2-enarate 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:

: 97506-01-9
(3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione

: 853799-31-2
1-ethyl 6-methyl (E)-4,5-di-O-benzyl-2,3-dideoxy-L-threo-hex-2-enarate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / 15 h

2.1: (i-Pr)2NEt / tetrahydrofuran / 2 h / -15 - 0 °C

3.1: NaBH₄ / methanol / 3 h / 0 °C

4.1: 35 percent / trichloroisocyanuric acid; TEMPO / tetrahydrofuran / -70 - -10 °C

5.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

5.2: 80 percent / tetrahydrofuran / 1 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; trichloroisocyanuric acid; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; 5.1: Wittig-Horner olefination / 5.2: Wittig-Horner olefination;
DOI:10.1002/hlca.200690066

Reference yield:

: 896448-10-5
(2R,3R)-2,3-Bis-benzyloxy-succinic acid monomethyl ester

: 853799-31-2
1-ethyl 6-methyl (E)-4,5-di-O-benzyl-2,3-dideoxy-L-threo-hex-2-enarate

Guidance literature:: Multi-step reaction with 4 steps

1.1: (i-Pr)2NEt / tetrahydrofuran / 2 h / -15 - 0 °C

2.1: NaBH₄ / methanol / 3 h / 0 °C

3.1: 35 percent / trichloroisocyanuric acid; TEMPO / tetrahydrofuran / -70 - -10 °C

4.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

4.2: 80 percent / tetrahydrofuran / 1 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; trichloroisocyanuric acid; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; 4.1: Wittig-Horner olefination / 4.2: Wittig-Horner olefination;
DOI:10.1002/hlca.200690066

Reference yield:

: (2R,3R)-2,3-Bis-benzyloxy-4-methoxycarbonyloxy-4-oxo-butyric acid methyl ester

: 853799-31-2
1-ethyl 6-methyl (E)-4,5-di-O-benzyl-2,3-dideoxy-L-threo-hex-2-enarate

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaBH₄ / methanol / 3 h / 0 °C

2.1: 35 percent / trichloroisocyanuric acid; TEMPO / tetrahydrofuran / -70 - -10 °C

3.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

3.2: 80 percent / tetrahydrofuran / 1 h

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; trichloroisocyanuric acid; sodium hydride; In tetrahydrofuran; methanol; 3.1: Wittig-Horner olefination / 3.2: Wittig-Horner olefination;
DOI:10.1002/hlca.200690066