(2R,3R,5S,8R,10S)-benzyl 2-((1R,3R)-1-(tert-butyldimethylsilyloxy)-6-iodo-3-methylhex-5-ynyl)-8,10-dimethyl-3-(triethylsilyloxy)-1-oxa-6-azaspiro[4.5]decane-6-carboxylate

Base Information

Chemical Name:(2R,3R,5S,8R,10S)-benzyl 2-((1R,3R)-1-(tert-butyldimethylsilyloxy)-6-iodo-3-methylhex-5-ynyl)-8,10-dimethyl-3-(triethylsilyloxy)-1-oxa-6-azaspiro[4.5]decane-6-carboxylate
CAS No.:896729-87-6
Molecular Formula:C₃₇H₆₂INO₅Si₂
Molecular Weight:783.978
Hs Code.:

(2R,3R,5S,8R,10S)-benzyl 2-((1R,3R)-1-(tert-butyldimethylsilyloxy)-6-iodo-3-methylhex-5-ynyl)-8,10-dimethyl-3-(triethylsilyloxy)-1-oxa-6-azaspiro[4.5]decane-6-carboxylate

Synonyms:(2R,3R,5S,8R,10S)-benzyl 2-((1R,3R)-1-(tert-butyldimethylsilyloxy)-6-iodo-3-methylhex-5-ynyl)-8,10-dimethyl-3-(triethylsilyloxy)-1-oxa-6-azaspiro[4.5]decane-6-carboxylate

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Chemical Property of (2R,3R,5S,8R,10S)-benzyl 2-((1R,3R)-1-(tert-butyldimethylsilyloxy)-6-iodo-3-methylhex-5-ynyl)-8,10-dimethyl-3-(triethylsilyloxy)-1-oxa-6-azaspiro[4.5]decane-6-carboxylate

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Technology Process of (2R,3R,5S,8R,10S)-benzyl 2-((1R,3R)-1-(tert-butyldimethylsilyloxy)-6-iodo-3-methylhex-5-ynyl)-8,10-dimethyl-3-(triethylsilyloxy)-1-oxa-6-azaspiro[4.5]decane-6-carboxylate

There total 13 articles about (2R,3R,5S,8R,10S)-benzyl 2-((1R,3R)-1-(tert-butyldimethylsilyloxy)-6-iodo-3-methylhex-5-ynyl)-8,10-dimethyl-3-(triethylsilyloxy)-1-oxa-6-azaspiro[4.5]decane-6-carboxylate 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: 95.0%

: 918310-80-2
(2R,3R,5S,8R,10S)-benzyl 2-((1R,3R)-1-(tert-butyldimethylsilyloxy)-3-methyl-6-(trimethylsilyl)hex-5-ynyl)-8,10-dimethyl-3-(triethylsilyloxy)-1-oxa-6-azaspiro[4.5]decane-6-carboxylate

: 896729-87-6
(2R,3R,5S,8R,10S)-benzyl 2-((1R,3R)-1-(tert-butyldimethylsilyloxy)-6-iodo-3-methylhex-5-ynyl)-8,10-dimethyl-3-(triethylsilyloxy)-1-oxa-6-azaspiro[4.5]decane-6-carboxylate

Guidance literature:: With N-iodo-succinimide; silver trifluoroacetate; In acetone; for 0.166667h;
DOI:10.1021/ja066971h

Reference yield: 87.0%

: (2R,3R,8R,10S)-2-[(1R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-triethylsilanyl-hex-5-ynyl]-8,10-dimethyl-3-triethylsilanyloxy-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid benzyl ester

: 896729-87-6
(2R,3R,5S,8R,10S)-benzyl 2-((1R,3R)-1-(tert-butyldimethylsilyloxy)-6-iodo-3-methylhex-5-ynyl)-8,10-dimethyl-3-(triethylsilyloxy)-1-oxa-6-azaspiro[4.5]decane-6-carboxylate

Guidance literature:: With N-iodo-succinimide; silver trifluoroacetate; In N,N-dimethyl-formamide; for 0.166667h;
DOI:10.1016/j.tet.2006.01.112

Reference yield:

: 896729-89-8
(3S,5R)-6-azido-3,5-dimethylhexan-2-one

: 896729-87-6
(2R,3R,5S,8R,10S)-benzyl 2-((1R,3R)-1-(tert-butyldimethylsilyloxy)-6-iodo-3-methylhex-5-ynyl)-8,10-dimethyl-3-(triethylsilyloxy)-1-oxa-6-azaspiro[4.5]decane-6-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran / 1 h / -78 °C

2.1: 66 percent / MgBr₂*OEt₂ / CH₂Cl₂ / -78 - -25 °C

3.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -10 °C

4.1: 82 percent / DDQ; phosphate buffer / CH₂Cl₂; 2-methyl-propan-2-ol; H₂O / 0.5 h

5.1: 75 percent / triethylphosphine / toluene / 14 h

6.1: 73 percent / K₂CO₃; molecular sieves 4 Angstroem / CH₂Cl₂ / 14 h

7.1: 87 percent / N-iodosuccinimide; silver(I) trifluoroacetate / dimethylformamide / 0.17 h

With 2,6-dimethylpyridine; N-iodo-succinimide; phosphate buffer; 4 A molecular sieve; sodium hexamethyldisilazane; silver trifluoroacetate; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; triethylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 2.1: Mukaiyama aldol reaction;
DOI:10.1016/j.tet.2006.01.112