(E)-6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4,5-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-undec-4-en-3-ulose

Base Information

Chemical Name:(E)-6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4,5-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-undec-4-en-3-ulose
CAS No.:220542-44-9
Molecular Formula:C₄₇H₅₅NO₉
Molecular Weight:777.955
Hs Code.:

Synonyms:(E)-6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4,5-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-undec-4-en-3-ulose

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Chemical Property of (E)-6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4,5-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-undec-4-en-3-ulose

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Technology Process of (E)-6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4,5-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-undec-4-en-3-ulose

There total 11 articles about (E)-6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4,5-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-undec-4-en-3-ulose 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: 81.0%

: 213828-81-0
6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-lyxo-D-manno/D-altro-3-undeculose

: 220542-44-9
(E)-6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4,5-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-undec-4-en-3-ulose

Guidance literature:: With 4 A molecular sieve; copper(II) bis(trifluoromethanesulfonate); dicyclohexyl-carbodiimide; In acetonitrile; at 20 ℃; for 1.08333h;
DOI:10.1021/jo981861h

Reference yield:

: 60538-19-4,79479-07-5,96099-84-2,113525-91-0
N-(tert-butoxycarbonyl)-l-threonine methyl ester

: 220542-44-9
(E)-6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4,5-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-undec-4-en-3-ulose

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / triethylamine; 4-(N,N-dimethylamino)pyridine / dimethylformamide / 1.5 h / 0 - 20 °C

2: 75 percent / LiAlH₄ / tetrahydrofuran / 0.83 h / -50 °C

3: 96 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 1.5 h / 0 - 20 °C

4: 96 percent / n-Bu₄NF*3H₂O / tetrahydrofuran / 6 h / 20 °C

5: 94 percent / 4-Angstroem molecular sieves; pyridinium chlorochromate / CH₂Cl₂ / 0.33 h / 20 °C

6: 82 percent / 4-Angstroem molecular sieves; triethylamine / CH₂Cl₂ / 1 h / -15 °C

7: 78 percent / 4-Angstroem molecular sieves; BF₃*Et₂O / CH₂Cl₂ / 0.83 h / -30 °C

8: 81 percent / 1,3-dicyclohexylcarbodiimide; 4-Angstroem molecular sieves; Cu(OTf)2 / acetonitrile / 1.08 h / 20 °C

With dmap; lithium aluminium tetrahydride; 4 A molecular sieve; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; copper(II) bis(trifluoromethanesulfonate); triethylamine; dicyclohexyl-carbodiimide; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: silylation / 2: Reduction / 3: Cyclization / 4: desilylation / 5: Oxidation / 6: silylation / 7: Mukaiyama condensation; desilylation / 8: Dehydration;
DOI:10.1021/jo981861h

Reference yield:

: 142729-69-9
(2S,3R)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate

: 220542-44-9
(E)-6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4,5-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-undec-4-en-3-ulose

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / LiAlH₄ / tetrahydrofuran / 0.83 h / -50 °C

2: 96 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 1.5 h / 0 - 20 °C

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

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

5: 82 percent / 4-Angstroem molecular sieves; triethylamine / CH₂Cl₂ / 1 h / -15 °C

6: 78 percent / 4-Angstroem molecular sieves; BF₃*Et₂O / CH₂Cl₂ / 0.83 h / -30 °C

7: 81 percent / 1,3-dicyclohexylcarbodiimide; 4-Angstroem molecular sieves; Cu(OTf)2 / acetonitrile / 1.08 h / 20 °C

With lithium aluminium tetrahydride; 4 A molecular sieve; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; copper(II) bis(trifluoromethanesulfonate); triethylamine; dicyclohexyl-carbodiimide; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; acetonitrile; 1: Reduction / 2: Cyclization / 3: desilylation / 4: Oxidation / 5: silylation / 6: Mukaiyama condensation; desilylation / 7: Dehydration;
DOI:10.1021/jo981861h