(-)-(3R,4R,6R,7R,8R)-8-benzyloxy-6,7-O-isopropylidene-2,3-diphenyl-5-oxa-2-aza-spiro[3.4]octan-1-one

Base Information

Chemical Name:(-)-(3R,4R,6R,7R,8R)-8-benzyloxy-6,7-O-isopropylidene-2,3-diphenyl-5-oxa-2-aza-spiro[3.4]octan-1-one
CAS No.:951250-91-2
Molecular Formula:C₂₈H₂₇NO₅
Molecular Weight:457.526
Hs Code.:

Synonyms:(-)-(3R,4R,6R,7R,8R)-8-benzyloxy-6,7-O-isopropylidene-2,3-diphenyl-5-oxa-2-aza-spiro[3.4]octan-1-one

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Chemical Property of (-)-(3R,4R,6R,7R,8R)-8-benzyloxy-6,7-O-isopropylidene-2,3-diphenyl-5-oxa-2-aza-spiro[3.4]octan-1-one

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Technology Process of (-)-(3R,4R,6R,7R,8R)-8-benzyloxy-6,7-O-isopropylidene-2,3-diphenyl-5-oxa-2-aza-spiro[3.4]octan-1-one

There total 6 articles about (-)-(3R,4R,6R,7R,8R)-8-benzyloxy-6,7-O-isopropylidene-2,3-diphenyl-5-oxa-2-aza-spiro[3.4]octan-1-one 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: 43.0%

: 153215-67-9
(-)-(2S,3R,4R,5R)-3-benzyloxy-4,5-O-isopropylidene-tetrahydro-furan-2-carboxylic acid chloride

: 1750-36-3,33993-35-0,538-51-2,137431-97-1,137432-04-3
(E)-N-benzylidenebenzenamine

: 951250-91-2
(-)-(3R,4R,6R,7R,8R)-8-benzyloxy-6,7-O-isopropylidene-2,3-diphenyl-5-oxa-2-aza-spiro[3.4]octan-1-one

: (-)-(3S,4S,6R,7R,8R)-8-benzyloxy-6,7-O-isopropylidene-2,3-diphenyl-5-oxa-2-aza-spiro[3.4]octan-1-one

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1016/j.tet.2007.06.073

Reference yield:

: 350255-13-9
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 951250-91-2
(-)-(3R,4R,6R,7R,8R)-8-benzyloxy-6,7-O-isopropylidene-2,3-diphenyl-5-oxa-2-aza-spiro[3.4]octan-1-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / NaH / dimethylformamide / 3 h / 0 - 20 °C

2.1: aq. CH₃COOH / 3 h / 70 °C

2.2: 78 percent / aq. NAIO₄; silica gel / CH₂Cl₂ / 2 h / 20 °C

3.1: 82 percent / AgNO₃; aq. KOH / 1 h / 20 °C

4.1: 92 percent / oxalyl chloride / CH₂Cl₂ / 5 h / Heating

5.1: 43 percent / triethylamine / CH₂Cl₂ / 20 °C

With potassium hydroxide; oxalyl dichloride; sodium hydride; silver nitrate; acetic acid; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 5.1: Staudinger cycloaddition;
DOI:10.1016/j.tet.2007.06.073

Reference yield:

: 39682-04-7
(3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolane-5-carboxylic acid

: 951250-91-2
(-)-(3R,4R,6R,7R,8R)-8-benzyloxy-6,7-O-isopropylidene-2,3-diphenyl-5-oxa-2-aza-spiro[3.4]octan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / oxalyl chloride / CH₂Cl₂ / 5 h / Heating

2: 43 percent / triethylamine / CH₂Cl₂ / 20 °C

With oxalyl dichloride; triethylamine; In dichloromethane; 2: Staudinger cycloaddition;
DOI:10.1016/j.tet.2007.06.073