(2S,3S,5R,8S,10R)-3-Benzoyloxy-2-[(1S,3S)-1-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyl]-8,10-dimethyl-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,3S,5R,8S,10R)-3-Benzoyloxy-2-[(1S,3S)-1-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyl]-8,10-dimethyl-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid tert-butyl ester
CAS No.:381214-17-1
Molecular Formula:C₃₇H₄₉NO₇
Molecular Weight:619.799
Hs Code.:

(2S,3S,5R,8S,10R)-3-Benzoyloxy-2-[(1S,3S)-1-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyl]-8,10-dimethyl-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid tert-butyl ester

Synonyms:(2S,3S,5R,8S,10R)-3-Benzoyloxy-2-[(1S,3S)-1-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyl]-8,10-dimethyl-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid tert-butyl ester

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Chemical Property of (2S,3S,5R,8S,10R)-3-Benzoyloxy-2-[(1S,3S)-1-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyl]-8,10-dimethyl-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid tert-butyl ester

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Technology Process of (2S,3S,5R,8S,10R)-3-Benzoyloxy-2-[(1S,3S)-1-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyl]-8,10-dimethyl-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid tert-butyl ester

There total 18 articles about (2S,3S,5R,8S,10R)-3-Benzoyloxy-2-[(1S,3S)-1-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyl]-8,10-dimethyl-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid tert-butyl ester 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: 72.0%

: Benzoic acid (2S,3S)-5-((1R,3S)-4-tert-butoxycarbonylamino-1,3-dimethyl-butyl)-5-methoxy-2-[(1S,3S)-1-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyl]-tetrahydro-furan-3-yl ester

: 381214-17-1
(2S,3S,5R,8S,10R)-3-Benzoyloxy-2-[(1S,3S)-1-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyl]-8,10-dimethyl-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid tert-butyl ester

Guidance literature:: ytterbium(III) triflate; In acetonitrile; at 20 ℃;
DOI:10.1002/1521-3773(20011001)40:19<3663::AID-ANIE3663>3.0.CO;2-U

Reference yield:

: 90270-02-3,97937-36-5
(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate

: 381214-17-1
(2S,3S,5R,8S,10R)-3-Benzoyloxy-2-[(1S,3S)-1-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyl]-8,10-dimethyl-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: Et₃N / CH₂Cl₂ / 20 °C

2.1: LiAlH₄ / diethyl ether / 0 °C

3.1: PPh₃; (PhO)2P(=O)N₃; DEAD / tetrahydrofuran / 20 °C

4.1: TBAF / tetrahydrofuran / 20 °C

5.1: DMSO; ClCOCOCl; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.2: tetrahydrofuran / 0 °C

5.3: 62 percent / DMSO; ClCOCOCl; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: LDA / tetrahydrofuran / -78 °C

7.1: TBAF; AcOH / tetrahydrofuran / 20 °C

8.1: PPTS / methanol / 20 °C

9.1: 62 percent / PPh₃; DEAD / tetrahydrofuran / 20 °C

10.1: 82 percent / Bu₃P / toluene / -20 - 20 °C

11.1: 72 percent / Yb[OTf]3 / acetonitrile / 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; tributylphosphine; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; ytterbium(III) triflate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; 9.1: Mitsunobu reaction;
DOI:10.1002/1521-3773(20011001)40:19<3663::AID-ANIE3663>3.0.CO;2-U

Reference yield:

: 147782-80-7
(2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol

: 381214-17-1
(2S,3S,5R,8S,10R)-3-Benzoyloxy-2-[(1S,3S)-1-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyl]-8,10-dimethyl-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: PPh₃; (PhO)2P(=O)N₃; DEAD / tetrahydrofuran / 20 °C

2.1: TBAF / tetrahydrofuran / 20 °C

3.1: DMSO; ClCOCOCl; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.2: tetrahydrofuran / 0 °C

3.3: 62 percent / DMSO; ClCOCOCl; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: LDA / tetrahydrofuran / -78 °C

5.1: TBAF; AcOH / tetrahydrofuran / 20 °C

6.1: PPTS / methanol / 20 °C

7.1: 62 percent / PPh₃; DEAD / tetrahydrofuran / 20 °C

8.1: 82 percent / Bu₃P / toluene / -20 - 20 °C

9.1: 72 percent / Yb[OTf]3 / acetonitrile / 20 °C

With oxalyl dichloride; tributylphosphine; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; ytterbium(III) triflate; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; 7.1: Mitsunobu reaction;
DOI:10.1002/1521-3773(20011001)40:19<3663::AID-ANIE3663>3.0.CO;2-U