(E)-5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-dec-3-enitol

Base Information

Chemical Name:(E)-5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-dec-3-enitol
CAS No.:246864-29-9
Molecular Formula:C₄₆H₅₅NO₈
Molecular Weight:749.945
Hs Code.:

Synonyms:(E)-5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-dec-3-enitol

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Chemical Property of (E)-5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-dec-3-enitol

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Technology Process of (E)-5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-dec-3-enitol

There total 9 articles about (E)-5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-dec-3-enitol 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: 37.0%

: 246864-28-8
(4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(sulfonylmethyl)-1,3-oxazolidine

: 246864-29-9
(E)-5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-dec-3-enitol

Guidance literature:: With aluminum oxide; potassium hydroxide; dibromodifluoromethane; In tert-butyl alcohol; at 60 ℃;
DOI:10.1039/a905014k

Reference yield:

: 246864-27-7
(S)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine

: 246864-29-9
(E)-5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-dec-3-enitol

Guidance literature:: Multi-step reaction with 3 steps

1: 71 percent / K₂CO₃ / acetone / 4.4 h / Heating

2: mCPBA; Na₂HPO₄ / CH₂Cl₂ / 3 h

3: 37 percent / KOH; Al₂O₃; CBr₂F₂ / CH₂Cl₂; 2-methyl-propan-2-ol / 60 °C

With aluminum oxide; potassium hydroxide; disodium hydrogenphosphate; dibromodifluoromethane; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetone; tert-butyl alcohol; 3: Ramberg-Baecklund rearrangement;
DOI:10.1002/1099-0690(200204)2002:7<1323::AID-EJOC1323>3.0.CO;2-8

Reference yield:

: 441044-67-3
(4S)-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1'-yl)-N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(thiomethyl)-1,3-oxazolidine

: 246864-29-9
(E)-5,9-andhydro-6,7,8,10-tetra-O-benzyl-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-2,3,4-trideoxy-D-erythro-L-talo-dec-3-enitol

Guidance literature:: Multi-step reaction with 2 steps

1: mCPBA; Na₂HPO₄ / CH₂Cl₂ / 3 h

2: 37 percent / KOH; Al₂O₃; CBr₂F₂ / CH₂Cl₂; 2-methyl-propan-2-ol / 60 °C

With aluminum oxide; potassium hydroxide; disodium hydrogenphosphate; dibromodifluoromethane; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; tert-butyl alcohol; 2: Ramberg-Baecklund rearrangement;
DOI:10.1002/1099-0690(200204)2002:7<1323::AID-EJOC1323>3.0.CO;2-8