(2'S,3'R,3'aR,6'aR,4aR,6aS)-6-benzyl-3'-benzyloxy-6-aza-3,5-dioxabicyclo[4.2.1]nonane-spiro-[1.2]-1',4',6'-trioxo-bicyclo[3.3.0]octane

Base Information

Chemical Name:(2'S,3'R,3'aR,6'aR,4aR,6aS)-6-benzyl-3'-benzyloxy-6-aza-3,5-dioxabicyclo[4.2.1]nonane-spiro-[1.2]-1',4',6'-trioxo-bicyclo[3.3.0]octane
CAS No.:952716-11-9
Molecular Formula:C₂₆H₃₁NO₆
Molecular Weight:453.535
Hs Code.:

Synonyms:(2'S,3'R,3'aR,6'aR,4aR,6aS)-6-benzyl-3'-benzyloxy-6-aza-3,5-dioxabicyclo[4.2.1]nonane-spiro-[1.2]-1',4',6'-trioxo-bicyclo[3.3.0]octane

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Chemical Property of (2'S,3'R,3'aR,6'aR,4aR,6aS)-6-benzyl-3'-benzyloxy-6-aza-3,5-dioxabicyclo[4.2.1]nonane-spiro-[1.2]-1',4',6'-trioxo-bicyclo[3.3.0]octane

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Technology Process of (2'S,3'R,3'aR,6'aR,4aR,6aS)-6-benzyl-3'-benzyloxy-6-aza-3,5-dioxabicyclo[4.2.1]nonane-spiro-[1.2]-1',4',6'-trioxo-bicyclo[3.3.0]octane

There total 5 articles about (2'S,3'R,3'aR,6'aR,4aR,6aS)-6-benzyl-3'-benzyloxy-6-aza-3,5-dioxabicyclo[4.2.1]nonane-spiro-[1.2]-1',4',6'-trioxo-bicyclo[3.3.0]octane 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:

: 952716-09-5
(3aR,4aR,5R,6R)-5-allyloxymethyl-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-tert-butyl-dimethyl-silane

: 952716-11-9
(2'S,3'R,3'aR,6'aR,4aR,6aS)-6-benzyl-3'-benzyloxy-6-aza-3,5-dioxabicyclo[4.2.1]nonane-spiro-[1.2]-1',4',6'-trioxo-bicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 3 steps

1: 75 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

2: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

3: 600 mg / ethanol / 26 h

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; 2: Swern oxidation;
DOI:10.1021/jo070846m

Reference yield:

: 952716-10-8
(3aR,4aR,5R,6R)-(5-allyloxymethyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methanol

: 952716-11-9
(2'S,3'R,3'aR,6'aR,4aR,6aS)-6-benzyl-3'-benzyloxy-6-aza-3,5-dioxabicyclo[4.2.1]nonane-spiro-[1.2]-1',4',6'-trioxo-bicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 2 steps

1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

2: 600 mg / ethanol / 26 h

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In ethanol; dichloromethane; 1: Swern oxidation;
DOI:10.1021/jo070846m

Reference yield:

: 952716-08-4
(3aR,4aR,5R,6R)-[6-benzyloxy-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyltetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol

: 952716-11-9
(2'S,3'R,3'aR,6'aR,4aR,6aS)-6-benzyl-3'-benzyloxy-6-aza-3,5-dioxabicyclo[4.2.1]nonane-spiro-[1.2]-1',4',6'-trioxo-bicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 4 steps

1: 83 percent / NaH / tetrahydrofuran / 4.5 h / Heating

2: 75 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

3: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

4: 600 mg / ethanol / 26 h

With oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; 3: Swern oxidation;
DOI:10.1021/jo070846m