(3S,4R,5R,6S,7S)-4-(Dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octane-1,3,8-triol

Base Information

Chemical Name:(3S,4R,5R,6S,7S)-4-(Dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octane-1,3,8-triol
CAS No.:136904-93-3
Molecular Formula:C₂₇H₃₉NO₇
Molecular Weight:489.609
Hs Code.:

Synonyms:(3S,4R,5R,6S,7S)-4-(Dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octane-1,3,8-triol

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Chemical Property of (3S,4R,5R,6S,7S)-4-(Dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octane-1,3,8-triol

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Technology Process of (3S,4R,5R,6S,7S)-4-(Dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octane-1,3,8-triol

There total 12 articles about (3S,4R,5R,6S,7S)-4-(Dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octane-1,3,8-triol 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%

: 136904-91-1,136983-67-0
(3S,4R,5R,6S,7S)-1,8-Bis<(tert-butyldimethylsilyl)oxy>-4-(dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octan-3-ol

: 136904-93-3
(3S,4R,5R,6S,7S)-4-(Dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octane-1,3,8-triol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Ambient temperature;
DOI:10.1021/jo00053a015

Reference yield:

: 108818-01-5
(2S,3R,4S,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol

: 136904-93-3
(3S,4R,5R,6S,7S)-4-(Dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octane-1,3,8-triol

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) triethylaluminum / 1.) CH₂Cl₂, hexane, 30 min, 2.) CH₂Cl₂, r.t., 14 h

2: 88 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 85 percent / N,N-diisopropylethylamine / CHCl₃ / 1 h / Heating

4: 91 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature

5: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -80 deg C, 2 h, 2.) -80 deg C to r.t.

6: 45 percent / TiCl₄, molecular sieves 4A / CH₂Cl₂ / 0.5 h / -80 °C

7: 81 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature

8: 83 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

9: 54 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 12 h / Heating

10: 86 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

11: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; triethylaluminum; titanium tetrachloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00053a015

Reference yield:

: 145625-35-0
(2R,3R,4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-2-(dibenzylamino)-4,5-(isopropylidenedioxy)-3-(methoxymethoxy)-hexan-1-ol

: 136904-93-3
(3S,4R,5R,6S,7S)-4-(Dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octane-1,3,8-triol

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -80 deg C, 2 h, 2.) -80 deg C to r.t.

2: 45 percent / TiCl₄, molecular sieves 4A / CH₂Cl₂ / 0.5 h / -80 °C

3: 81 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature

4: 83 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

5: 54 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 12 h / Heating

6: 86 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

7: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00053a015