methyl (αS,3S)-13-azido-α-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methyl]-12-oxo-1,6-dioxa-11-azadispiro[4.2.6.2]hexadecane-11-acetate

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Chemical Name:methyl (αS,3S)-13-azido-α-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methyl]-12-oxo-1,6-dioxa-11-azadispiro[4.2.6.2]hexadecane-11-acetate
CAS No.:264271-57-0
Molecular Formula:C₂₈H₃₈N₄O₆
Molecular Weight:526.633
Hs Code.:

Synonyms:methyl (αS,3S)-13-azido-α-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methyl]-12-oxo-1,6-dioxa-11-azadispiro[4.2.6.2]hexadecane-11-acetate

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Chemical Property of methyl (αS,3S)-13-azido-α-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methyl]-12-oxo-1,6-dioxa-11-azadispiro[4.2.6.2]hexadecane-11-acetate

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Technology Process of methyl (αS,3S)-13-azido-α-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methyl]-12-oxo-1,6-dioxa-11-azadispiro[4.2.6.2]hexadecane-11-acetate

There total 2 articles about methyl (αS,3S)-13-azido-α-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methyl]-12-oxo-1,6-dioxa-11-azadispiro[4.2.6.2]hexadecane-11-acetate 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: 79.0%

: (S)-3-[4-(3-Methyl-but-2-enyloxy)-phenyl]-2-[2-oxo-3-(toluene-4-sulfonyloxy)-9,14-dioxa-1-aza-dispiro[4.2.6.2]hexadec-1-yl]-propionic acid methyl ester

: 264271-57-0
methyl (αS,3S)-13-azido-α-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methyl]-12-oxo-1,6-dioxa-11-azadispiro[4.2.6.2]hexadecane-11-acetate

: methyl (αS,13R)-13-azido-α-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methyl]-12-oxo-1,6-dioxa-11-azadispiro[4.2.6.2]hexadecane-11-acetate

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 25 ℃; for 12h;
DOI:10.1021/ol991401q

Reference yield:

: methyl (αS)-13-hydroxy-α-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methyl]-12-oxo-1,6-dioxa-11-azadispiro[4.2.6.2]hexadecane-11-acetate

: 264271-57-0
methyl (αS,3S)-13-azido-α-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methyl]-12-oxo-1,6-dioxa-11-azadispiro[4.2.6.2]hexadecane-11-acetate

Guidance literature:: Multi-step reaction with 2 steps

1: Et₃N; DMAP / CH₂Cl₂ / 6 h / 25 °C

2: 79 percent / NaN₃ / dimethylformamide / 12 h / 25 °C

With dmap; sodium azide; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1: Tosylation / 2: Substitution;
DOI:10.1021/ol991401q

Reference yield:

: 264271-57-0
methyl (αS,3S)-13-azido-α-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methyl]-12-oxo-1,6-dioxa-11-azadispiro[4.2.6.2]hexadecane-11-acetate

: (1S,1'S,2'Z,3R,5'S)-3-hydroxy-4'-methyl-2'-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methylene]-spiro[cyclohexane-1,7'-[1,4]diazabicyclo[3.2.1]octan]-4-one

Guidance literature:: Multi-step reaction with 9 steps

1: LiAlH₄ / tetrahydrofuran / 2 h / Heating

2: tetrahydrofuran / 0.5 h / 25 °C

3: 207 mg / LiAlH₄ / tetrahydrofuran / 2 h / Heating

4: Et₃N; DMSO / CH₂Cl₂ / -78 - 0 °C

5: 18 mg / K₂CO₃; H₂O / methanol / 2 h / 25 °C

6: DDQ / CH₂Cl₂ / 2 h / 25 °C

7: 11 mg / NaCNBH₃; AcOH / methanol / 1 h / 25 °C

8: 89 percent / aq. HCl / acetone / 3 h / 25 °C

9: (1S)-10-(camphorsulfonyl)oxaziridine / tetrahydrofuran / 0.33 h

With hydrogenchloride; lithium aluminium tetrahydride; water; sodium cyanoborohydride; (1S)-(+)-(10-camphorsulfonyl)-oxaziridine; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; acetone; 1: Reduction / 2: Formylation / 3: Reduction / 4: Oxidation / 5: Hydrolysis / 6: Oxidation / 7: Reduction / 8: Hydrolysis / 9: Oxidation;
DOI:10.1021/ol991401q