7-acetamido-6,10-anhydro-8,9,11-tri-O-benzyl-2,3,4,5,7-pentadeoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undeconic acid

Base Information

Chemical Name:7-acetamido-6,10-anhydro-8,9,11-tri-O-benzyl-2,3,4,5,7-pentadeoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undeconic acid
CAS No.:287962-67-8
Molecular Formula:C₃₉H₅₀N₂O₉
Molecular Weight:690.834
Hs Code.:

Synonyms:7-acetamido-6,10-anhydro-8,9,11-tri-O-benzyl-2,3,4,5,7-pentadeoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undeconic acid

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Chemical Property of 7-acetamido-6,10-anhydro-8,9,11-tri-O-benzyl-2,3,4,5,7-pentadeoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undeconic acid

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Technology Process of 7-acetamido-6,10-anhydro-8,9,11-tri-O-benzyl-2,3,4,5,7-pentadeoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undeconic acid

There total 8 articles about 7-acetamido-6,10-anhydro-8,9,11-tri-O-benzyl-2,3,4,5,7-pentadeoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undeconic acid 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: 87.0%

: 443916-17-4
7-acetamido-6,10-anhydro-8,9,11-tri-O-benzyl-2,3,4,5,7-pentadeoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undecitol

: 287962-67-8
7-acetamido-6,10-anhydro-8,9,11-tri-O-benzyl-2,3,4,5,7-pentadeoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undeconic acid

Guidance literature:: With chromium(VI) oxide; sulfuric acid; In acetone; at 0 - 20 ℃; for 3h;
DOI:10.1021/jo020054m

Reference yield:

: 287962-79-2
4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-L-gluco-oct-1-ynitol

: 287962-67-8
7-acetamido-6,10-anhydro-8,9,11-tri-O-benzyl-2,3,4,5,7-pentadeoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undeconic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 52 percent / LiHMDS / tetrahydrofuran; hexane / 3 h / -45 °C

2: 85 percent / p-toluenesulfonylhydrazide; aq. AcONa / 1,2-dimethoxy-ethane / 5.5 h / 85 °C

3: 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 5 h / 70 °C

4: 60 percent / Bu₃SnH; AIBN / toluene / 2 h / 85 °C

5: 87 percent / CrO₃; aq. H₂SO₄ / acetone / 3 h / 0 - 20 °C

With chromium(VI) oxide; dmap; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; sodium acetate; toluene-4-sulfonic acid hydrazide; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; acetone; toluene; 4: Barton-McCombie reaction / 5: Jones oxidation;
DOI:10.1021/jo020054m

Reference yield:

: 443916-54-9
(R)-4-[3-((2R,3S,4R,5R,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-hydroxy-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 287962-67-8
7-acetamido-6,10-anhydro-8,9,11-tri-O-benzyl-2,3,4,5,7-pentadeoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-undeconic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 5 h / 70 °C

2: 60 percent / Bu₃SnH; AIBN / toluene / 2 h / 85 °C

3: 87 percent / CrO₃; aq. H₂SO₄ / acetone / 3 h / 0 - 20 °C

With chromium(VI) oxide; dmap; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; In tetrahydrofuran; acetone; toluene; 2: Barton-McCombie reaction / 3: Jones oxidation;
DOI:10.1021/jo020054m