6-ethyl 2,3-di-O-benzyl-5-O-[(trifluoromethyl)sulfonyl]-D-galactarate-1,4-lactone

Base Information

Chemical Name:6-ethyl 2,3-di-O-benzyl-5-O-[(trifluoromethyl)sulfonyl]-D-galactarate-1,4-lactone
CAS No.:853799-41-4
Molecular Formula:C₂₃H₂₃F₃O₉S
Molecular Weight:532.491
Hs Code.:

Synonyms:6-ethyl 2,3-di-O-benzyl-5-O-[(trifluoromethyl)sulfonyl]-D-galactarate-1,4-lactone

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Chemical Property of 6-ethyl 2,3-di-O-benzyl-5-O-[(trifluoromethyl)sulfonyl]-D-galactarate-1,4-lactone

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Technology Process of 6-ethyl 2,3-di-O-benzyl-5-O-[(trifluoromethyl)sulfonyl]-D-galactarate-1,4-lactone

There total 7 articles about 6-ethyl 2,3-di-O-benzyl-5-O-[(trifluoromethyl)sulfonyl]-D-galactarate-1,4-lactone 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: 94.0%

: 853799-40-3
6-ethyl 2,3-di-O-benzyl-D-galactarate-1,4-lactone

: 358-23-6
trifluoromethylsulfonic anhydride

: 853799-41-4
6-ethyl 2,3-di-O-benzyl-5-O-[(trifluoromethyl)sulfonyl]-D-galactarate-1,4-lactone

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 - 0 ℃;
DOI:10.1016/j.tetlet.2005.03.188

Reference yield:

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

: 853799-41-4
6-ethyl 2,3-di-O-benzyl-5-O-[(trifluoromethyl)sulfonyl]-D-galactarate-1,4-lactone

Guidance literature:: Multi-step reaction with 7 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

6.1: 87 percent / N-methylmorpholine N-oxide monohydrate; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 36 h

7.1: 94 percent / CH₂Cl₂ / -78 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; osmium(VIII) oxide; trichloroisocyanuric acid; sodium hydride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol; 5.1: Wittig-Horner olefination / 5.2: Wittig-Horner olefination;
DOI:10.1002/hlca.200690066

Reference yield:

: 853799-30-1
4-methyl 2,3-di-O-benzyl-L-threouronate

: 853799-41-4
6-ethyl 2,3-di-O-benzyl-5-O-[(trifluoromethyl)sulfonyl]-D-galactarate-1,4-lactone

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 80 percent / tetrahydrofuran / 1 h

2.1: 87 percent / N-methylmorpholine N-oxide monohydrate; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 36 h

3.1: 94 percent / CH₂Cl₂ / -78 °C

With osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; acetone; tert-butyl alcohol; 1.1: Wittig-Horner olefination / 1.2: Wittig-Horner olefination;
DOI:10.1002/hlca.200690066