5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-deconic acid

Base Information

Chemical Name:5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-deconic acid
CAS No.:213819-86-4
Molecular Formula:C₄₃H₅₁NO₉
Molecular Weight:725.879
Hs Code.:

Synonyms:5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-deconic acid

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Chemical Property of 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-deconic acid

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Technology Process of 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-deconic acid

There total 14 articles about 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-deconic 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: 95.0%

: 213820-05-4
5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-decitol

: 213819-86-4
5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-deconic acid

Guidance literature:: With jones reagent; In acetone; at 0 - 20 ℃; for 3.5h;
DOI:10.1021/jo981861h

Reference yield:

: 213820-05-4
5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-decitol

: [(S)-1-Hydroxymethyl-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-carbamic acid tert-butyl ester

: 213819-86-4
5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-deconic acid

Guidance literature:: With jones reagent; In acetone; at 0 - 20 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1039/a800571k

Reference yield:

: 152491-86-6
tert-butyl ((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-1-hydroxybutan-2-yl)carbamate

: 213819-86-4
5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-deconic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 96 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 1.5 h / 0 - 20 °C

2: 96 percent / n-Bu₄NF*3H₂O / tetrahydrofuran / 6 h / 20 °C

3: 94 percent / 4-Angstroem molecular sieves; pyridinium chlorochromate / CH₂Cl₂ / 0.33 h / 20 °C

4: 82 percent / 4-Angstroem molecular sieves; triethylamine / CH₂Cl₂ / 1 h / -15 °C

5: 24 percent / ZnBr₂ / CH₂Cl₂ / 5 h / -15 °C

6: NaBH₄ / methanol; diethyl ether / 1 h / -20 °C

7: 83 percent / 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 6 h / 70 °C

8: 293 mg / Bu₃SnH; AIBN / toluene / 2 h / 85 °C

9: 95 percent / Jones reagent / acetone / 3.5 h / 0 - 20 °C

With dmap; sodium tetrahydroborate; jones reagent; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; triethylamine; pyridinium chlorochromate; zinc dibromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene; 1: Cyclization / 2: desilylation / 3: Oxidation / 4: silylation / 5: glycosylation / 6: Reduction / 7: Esterification / 8: Reduction / 9: Ring cleavage;
DOI:10.1021/jo981861h