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-erythro-L-gulo-undecitol

Base Information

Chemical Name: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-erythro-L-gulo-undecitol
CAS No.:443916-20-9
Molecular Formula:C₄₂H₅₆N₂O₈
Molecular Weight:716.915
Hs Code.:

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-erythro-L-gulo-undecitol

Synonyms: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-erythro-L-gulo-undecitol

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Chemical Property of 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-erythro-L-gulo-undecitol

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Technology Process of 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-erythro-L-gulo-undecitol

There total 4 articles about 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-erythro-L-gulo-undecitol 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: 78.0%

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

: 443916-20-9
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-erythro-L-gulo-undecitol

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 85 ℃; for 2h;
DOI:10.1021/jo020054m

Reference yield:

: 443916-44-7
4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-oct-1-ynitol

: 443916-20-9
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-erythro-L-gulo-undecitol

Guidance literature:: Multi-step reaction with 4 steps

1: 64 percent / LiHMDS / tetrahydrofuran; hexane / 3 h / -45 °C

2: 97 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: 78 percent / Bu₃SnH; AIBN / toluene / 2 h / 85 °C

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

Reference yield:

: 443916-49-2
(R)-4-[3-((2R,3S,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-hydroxy-prop-2-ynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 443916-20-9
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-erythro-L-gulo-undecitol

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / p-toluenesulfonylhydrazide; aq. AcONa / 1,2-dimethoxy-ethane / 5.5 h / 85 °C

2: 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 5 h / 70 °C

3: 78 percent / Bu₃SnH; AIBN / toluene / 2 h / 85 °C

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium acetate; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; 1,2-dimethoxyethane; toluene; 3: Barton-McCombie reaction;
DOI:10.1021/jo020054m