(1R,5S,8S,9R)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

Base Information

Chemical Name:(1R,5S,8S,9R)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol
CAS No.:874947-13-4
Molecular Formula:C₂₂H₃₇NO₄Si
Molecular Weight:407.626
Hs Code.:

Synonyms:(1R,5S,8S,9R)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

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Chemical Property of (1R,5S,8S,9R)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

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Technology Process of (1R,5S,8S,9R)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

There total 5 articles about (1R,5S,8S,9R)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol 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: 78.0%

: 4-nitrobenzoic acid (1R,5S,8S,9R)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]non-9-yl ester

: 874947-13-4
(1R,5S,8S,9R)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

Guidance literature:: With sodium azide; In methanol; at 55 ℃; for 48h;
DOI:10.1002/anie.200501127

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 874947-13-4
(1R,5S,8S,9R)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: CH₂Cl₂ / 20 h / 20 °C

1.2: 100 percent / triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 97 percent / NaBH₄ / ethanol / 4 h / 20 °C

3.1: 81 percent / diethyl azodicarboxylate; triphenylphosphine / benzene / 6 h / 20 °C

4.1: 78 percent / NaN₃ / methanol / 48 h / 55 °C

With sodium tetrahydroborate; sodium azide; triphenylphosphine; diethylazodicarboxylate; In methanol; ethanol; dichloromethane; benzene; 3.1: Mitsunobu reaction;
DOI:10.1002/anie.200501127

Reference yield:

: 444307-99-7
(1R,5S,8S,9S)-2-benzyl-8-(tert-butyldimethylsilyloxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

: 874947-13-4
(1R,5S,8S,9R)-2-benzyl-8-(tert-butyldimethylsiloxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / diethyl azodicarboxylate; triphenylphosphine / benzene / 6 h / 20 °C

2: 78 percent / NaN₃ / methanol / 48 h / 55 °C

With sodium azide; triphenylphosphine; diethylazodicarboxylate; In methanol; benzene; 1: Mitsunobu reaction;
DOI:10.1002/anie.200501127