(2S,4R,7R,8R,9S,11S)-1-Azido-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-9-(4-methoxy-benzyloxy)-2,4,11-trimethyl-14-triethylsilanyl-tetradec-13-yn-5-one

Base Information

• Chemical Name: (2S,4R,7R,8R,9S,11S)-1-Azido-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-9-(4-methoxy-benzyloxy)-2,4,11-trimethyl-14-triethylsilanyl-tetradec-13-yn-5-one
• CAS No.: 381214-07-9
• Molecular Formula: C₃₇H₆₅N₃O₅Si₂
• Molecular Weight: 688.111

Synonyms:(2S,4R,7R,8R,9S,11S)-1-Azido-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-9-(4-methoxy-benzyloxy)-2,4,11-trimethyl-14-triethylsilanyl-tetradec-13-yn-5-one

Chemical Property of (2S,4R,7R,8R,9S,11S)-1-Azido-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-9-(4-methoxy-benzyloxy)-2,4,11-trimethyl-14-triethylsilanyl-tetradec-13-yn-5-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2S,4R,7R,8R,9S,11S)-1-Azido-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-9-(4-methoxy-benzyloxy)-2,4,11-trimethyl-14-triethylsilanyl-tetradec-13-yn-5-one

There total 13 articles about (2S,4R,7R,8R,9S,11S)-1-Azido-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-9-(4-methoxy-benzyloxy)-2,4,11-trimethyl-14-triethylsilanyl-tetradec-13-yn-5-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:

(3R,5S)-6-Azido-3,5-dimethyl-hexan-2-one (343782-86-5) + (2S,3S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-5-methyl-8-triethylsilanyl-oct-7-ynal (381214-08-0) → (2S,4R,7R,8R,9S,11S)-1-Azido-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-9-(4-methoxy-benzyloxy)-2,4,11-trimethyl-14-triethylsilanyl-tetradec-13-yn-5-one (381214-07-9) + (2S,4R,7S,8R,9S,11S)-1-Azido-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-9-(4-methoxy-benzyloxy)-2,4,11-trimethyl-14-triethylsilanyl-tetradec-13-yn-5-one

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; Title compound not separated from byproducts;

DOI:10.1002/1521-3773(20011001)40:19<3663::AID-ANIE3663>3.0.CO;2-U

Reference yield:

triethylsilyl chloride (994-30-9) → (2S,4R,7R,8R,9S,11S)-1-Azido-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-9-(4-methoxy-benzyloxy)-2,4,11-trimethyl-14-triethylsilanyl-tetradec-13-yn-5-one (381214-07-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-BuLi / tetrahydrofuran / -78 °C

2.1: PPTS / methanol / 20 °C

3.1: TPAP; NMO; 4 Angstroem MS / CH₂Cl₂ / 20 °C

4.1: (cyclohexyl)2BCl; Et₃N / diethyl ether

5.1: 87 percent / BF₃*OEt₂ / CH₂Cl₂ / 20 °C

6.1: NaBH₄ / methanol / 20 °C

6.2: EtMgBr / tetrahydrofuran / 0 °C

6.3: NaIO₄ / methanol; H₂O / 20 °C

7.1: LDA / tetrahydrofuran / -78 °C

With sodium tetrahydroborate; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 Angstroem MS; boron trifluoride diethyl etherate; dicyclohexylboron chloride; pyridinium p-toluenesulfonate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1002/1521-3773(20011001)40:19<3663::AID-ANIE3663>3.0.CO;2-U

Reference yield:

(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate (90270-02-3,97937-36-5) → (2S,4R,7R,8R,9S,11S)-1-Azido-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-9-(4-methoxy-benzyloxy)-2,4,11-trimethyl-14-triethylsilanyl-tetradec-13-yn-5-one (381214-07-9)

Guidance literature:

Multi-step reaction with 6 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

With lithium aluminium tetrahydride; oxalyl dichloride; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/1521-3773(20011001)40:19<3663::AID-ANIE3663>3.0.CO;2-U

upstream raw materials:

(3R,5S)-6-Azido-3,5-dimethyl-hexan-2-one

(2S,3S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-5-methyl-8-triethylsilanyl-oct-7-ynal

triethylsilyl chloride

(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate

Downstream raw materials:

(2R,3R)-5-((1R,3S)-4-Azido-1,3-dimethyl-butyl)-5-methoxy-2-[(1S,3S)-1-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyl]-tetrahydro-furan-3-ol

(2S,3S,5R,8S,10R)-3-(tert-Butyl-dimethyl-silanyloxy)-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

(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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