6-ethyl 5-azido-2,3-di-O-benzyl-5-deoxy-D-glucarate-1,4-lactone

Base Information

Chemical Name:6-ethyl 5-azido-2,3-di-O-benzyl-5-deoxy-D-glucarate-1,4-lactone
CAS No.:853799-37-8
Molecular Formula:C₂₂H₂₃N₃O₆
Molecular Weight:425.441
Hs Code.:

Synonyms:6-ethyl 5-azido-2,3-di-O-benzyl-5-deoxy-D-glucarate-1,4-lactone

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Chemical Property of 6-ethyl 5-azido-2,3-di-O-benzyl-5-deoxy-D-glucarate-1,4-lactone

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Technology Process of 6-ethyl 5-azido-2,3-di-O-benzyl-5-deoxy-D-glucarate-1,4-lactone

There total 8 articles about 6-ethyl 5-azido-2,3-di-O-benzyl-5-deoxy-D-glucarate-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: 98.0%

: 853799-36-7
6-ethyl 2,3-di-O-benzyl-5-O-[(trifluoromethyl)sulfonyl]-L-idarate-1,4-lactone

: 853799-37-8
6-ethyl 5-azido-2,3-di-O-benzyl-5-deoxy-D-glucarate-1,4-lactone

Guidance literature:: With N,N,N',N'-tetramethylguanidinium azide; In dichloromethane; at -90 - 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

: 853799-37-8
6-ethyl 5-azido-2,3-di-O-benzyl-5-deoxy-D-glucarate-1,4-lactone

Guidance literature:: Multi-step reaction with 8 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: 75 percent / (DHQ)2PHAL; K₃[Fe(CN)6]; K₂CO₃ / MeSO₂NH₂; OsO₄ / H₂O; 2-methyl-propan-2-ol / 6 h / 0 - 5 °C

7.1: 93 percent / CH₂Cl₂ / 0.08 h / -78 °C

8.1: 98 percent / tetramethylguanidinium azide / CH₂Cl₂ / 3 h / -90 - 10 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; Hydroquinone 1,4-phthalazinediyl diether; trichloroisocyanuric acid; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; tetramethylguanidinum azide; potassium hexacyanoferrate(III); osmium(VIII) oxide; methanesulfonamide; In tetrahydrofuran; methanol; dichloromethane; water; 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

: 853799-37-8
6-ethyl 5-azido-2,3-di-O-benzyl-5-deoxy-D-glucarate-1,4-lactone

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 80 percent / tetrahydrofuran / 1 h

2.1: 75 percent / (DHQ)2PHAL; K₃[Fe(CN)6]; K₂CO₃ / MeSO₂NH₂; OsO₄ / H₂O; 2-methyl-propan-2-ol / 6 h / 0 - 5 °C

3.1: 93 percent / CH₂Cl₂ / 0.08 h / -78 °C

4.1: 98 percent / tetramethylguanidinium azide / CH₂Cl₂ / 3 h / -90 - 10 °C

With Hydroquinone 1,4-phthalazinediyl diether; sodium hydride; potassium carbonate; tetramethylguanidinum azide; potassium hexacyanoferrate(III); osmium(VIII) oxide; methanesulfonamide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 1.1: Wittig-Horner olefination / 1.2: Wittig-Horner olefination;
DOI:10.1002/hlca.200690066