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

Base Information

Chemical Name:6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-arabino-D-manno/D-altro-3-undeculose
CAS No.:213828-84-3
Molecular Formula:C₄₇H₅₇NO₁₀
Molecular Weight:795.97
Hs Code.:

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

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Chemical Property of 6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-arabino-D-manno/D-altro-3-undeculose

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Technology Process of 6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-arabino-D-manno/D-altro-3-undeculose

There total 9 articles about 6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-arabino-D-manno/D-altro-3-undeculose 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: 70.0%

: 113019-43-5,140397-45-1,140397-46-2,140397-47-3,140397-49-5,91738-17-9
2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose

: 213819-91-1
(4R)-2,2-dimethyl-N-(tert-butoxycarbonyl)-4-(1-trimethylsilyloxyvinyl)-1,3-oxazolidine

: 167102-63-8,433683-01-3
(R)-N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-oxo-2-butanone

: 213828-84-3
6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-arabino-D-manno/D-altro-3-undeculose

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -30 ℃; for 0.833333h;
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

: 213828-84-3
6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-arabino-D-manno/D-altro-3-undeculose

Guidance literature:: Multi-step reaction with 7 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: 70 percent / 4-Angstroem molecular sieves; BF₃*Et₂O / CH₂Cl₂ / 0.83 h / -30 °C

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

Reference yield:

: 99216-67-8,766514-03-8
2-<<(tert-butoxy)carbonyl>amino>butane-1,3-diol

: 213828-84-3
6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-arabino-D-manno/D-altro-3-undeculose

Guidance literature:: Multi-step reaction with 4 steps

1: 10-camphorsulfonic acid / dimethylformamide / 0.5 h / 0 °C

2: 94 percent / 4-Angstroem molecular sieves; pyridinium chlorochromate / CH₂Cl₂ / 0.33 h / 20 °C

3: 82 percent / 4-Angstroem molecular sieves; triethylamine / CH₂Cl₂ / 1 h / -15 °C

4: 70 percent / 4-Angstroem molecular sieves; BF₃*Et₂O / CH₂Cl₂ / 0.83 h / -30 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; triethylamine; pyridinium chlorochromate; In dichloromethane; N,N-dimethyl-formamide; 1: Cyclization / 2: Oxidation / 3: silylation / 4: Mukaiyama condensation; desilylation;
DOI:10.1021/jo981861h