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

Base Information

Chemical Name:5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-decitol
CAS No.:220542-39-2
Molecular Formula:C₄₆H₅₇NO₈
Molecular Weight:751.96
Hs Code.:

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

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Chemical Property of 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-decitol

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Technology Process of 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-decitol

There total 3 articles about 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-decitol 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:

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

: 220542-39-2
5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-decitol

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 85 ℃; for 2h;
DOI:10.1021/jo981861h

Reference yield:

: (R)-4-[1-Hydroxy-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 220542-39-2
5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-decitol

Guidance literature:: Multi-step reaction with 2 steps

1: 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 6 h / 70 °C

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

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; toluene; 1: Esterification / 2: Reduction;
DOI:10.1021/jo981861h

Reference yield:

: 220542-32-5
5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-3-deculose

: 220542-39-2
5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-decitol

Guidance literature:: Multi-step reaction with 3 steps

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

2: 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 6 h / 70 °C

3: 293 mg / Bu₃SnH; AIBN / toluene / 2 h / 85 °C

With dmap; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; methanol; diethyl ether; toluene; 1: Reduction / 2: Esterification / 3: Reduction;
DOI:10.1021/jo981861h