(3S,4S,5R,6S)-4-benzyloxy-5-tert-butoxycarbonylamino-6-tert-butyldimethylsiloxymethyl-2,2-dimethyltetrahydropyran-3-carboxylic acid

Base Information

Chemical Name:(3S,4S,5R,6S)-4-benzyloxy-5-tert-butoxycarbonylamino-6-tert-butyldimethylsiloxymethyl-2,2-dimethyltetrahydropyran-3-carboxylic acid
CAS No.:954502-32-0
Molecular Formula:C₂₇H₄₅NO₇Si
Molecular Weight:523.742
Hs Code.:

Synonyms:(3S,4S,5R,6S)-4-benzyloxy-5-tert-butoxycarbonylamino-6-tert-butyldimethylsiloxymethyl-2,2-dimethyltetrahydropyran-3-carboxylic acid

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Chemical Property of (3S,4S,5R,6S)-4-benzyloxy-5-tert-butoxycarbonylamino-6-tert-butyldimethylsiloxymethyl-2,2-dimethyltetrahydropyran-3-carboxylic acid

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Technology Process of (3S,4S,5R,6S)-4-benzyloxy-5-tert-butoxycarbonylamino-6-tert-butyldimethylsiloxymethyl-2,2-dimethyltetrahydropyran-3-carboxylic acid

There total 5 articles about (3S,4S,5R,6S)-4-benzyloxy-5-tert-butoxycarbonylamino-6-tert-butyldimethylsiloxymethyl-2,2-dimethyltetrahydropyran-3-carboxylic acid 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: 87.0%

: 954502-31-9
(1S,4S,5R,8S)-8-benzyloxy-4-(tert-butyldimethylsiloxymethyl)-2,2-dimethyl-7-oxo-3-oxa-6-azabicyclo[3.2.1]octane-6-carboxylic acid tert-butyl ester

: 954502-32-0
(3S,4S,5R,6S)-4-benzyloxy-5-tert-butoxycarbonylamino-6-tert-butyldimethylsiloxymethyl-2,2-dimethyltetrahydropyran-3-carboxylic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 12h;
DOI:10.1055/s-2007-984907

Reference yield:

: 954502-28-4
(1R,5S,8S,9S)-2-benzyl-9-benzyloxy-8-(tert-butyldimethylsiloxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonane

: 954502-32-0
(3S,4S,5R,6S)-4-benzyloxy-5-tert-butoxycarbonylamino-6-tert-butyldimethylsiloxymethyl-2,2-dimethyltetrahydropyran-3-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 73 percent / H₂ / Pd/C / methanol / 12 h / 20 °C

2: 79 percent / PDC; Ac₂O / dimethylformamide / 12 h / 20 °C

3: 87 percent / LiOH / tetrahydrofuran; H₂O / 12 h / 20 °C

With lithium hydroxide; dipyridinium dichromate; hydrogen; acetic anhydride; palladium on activated charcoal; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;
DOI:10.1055/s-2007-984907

Reference yield:

: 870461-00-0
(1S,5R,8S)-2-benzyl-8-(tert-butyldimethylsilyloxymethyl)-6,6-dimethyl-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one

: 954502-32-0
(3S,4S,5R,6S)-4-benzyloxy-5-tert-butoxycarbonylamino-6-tert-butyldimethylsiloxymethyl-2,2-dimethyltetrahydropyran-3-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1: NaBH₄

2: 73 percent / H₂ / Pd/C / methanol / 12 h / 20 °C

3: 79 percent / PDC; Ac₂O / dimethylformamide / 12 h / 20 °C

4: 87 percent / LiOH / tetrahydrofuran; H₂O / 12 h / 20 °C

With lithium hydroxide; sodium tetrahydroborate; dipyridinium dichromate; hydrogen; acetic anhydride; palladium on activated charcoal; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;
DOI:10.1055/s-2007-984907