cyclo-[N-(tert-butyloxycarbonyl)-O-[[N-[(2S,3R,4S)-4-[(1S,2S,3S)-3-amino-2-benzyloxycyclohexanecarbonyl]oxy-3-(methoxymethoxy)-2,5-dimethylhexanoyl]-L-leucyl]-L-prolyl-N,O-dimethyl-L-tyrosyl]-L-threonyl]

Base Information

• Chemical Name: cyclo-[N-(tert-butyloxycarbonyl)-O-[[N-[(2S,3R,4S)-4-[(1S,2S,3S)-3-amino-2-benzyloxycyclohexanecarbonyl]oxy-3-(methoxymethoxy)-2,5-dimethylhexanoyl]-L-leucyl]-L-prolyl-N,O-dimethyl-L-tyrosyl]-L-threonyl]
• CAS No.: 339570-96-6
• Molecular Formula: C₅₅H₈₁N₅O₁₄
• Molecular Weight: 1036.27

Synonyms:

Chemical Property of cyclo-[N-(tert-butyloxycarbonyl)-O-[[N-[(2S,3R,4S)-4-[(1S,2S,3S)-3-amino-2-benzyloxycyclohexanecarbonyl]oxy-3-(methoxymethoxy)-2,5-dimethylhexanoyl]-L-leucyl]-L-prolyl-N,O-dimethyl-L-tyrosyl]-L-threonyl]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cyclo-[N-(tert-butyloxycarbonyl)-O-[[N-[(2S,3R,4S)-4-[(1S,2S,3S)-3-amino-2-benzyloxycyclohexanecarbonyl]oxy-3-(methoxymethoxy)-2,5-dimethylhexanoyl]-L-leucyl]-L-prolyl-N,O-dimethyl-L-tyrosyl]-L-threonyl]

There total 23 articles about cyclo-[N-(tert-butyloxycarbonyl)-O-[[N-[(2S,3R,4S)-4-[(1S,2S,3S)-3-amino-2-benzyloxycyclohexanecarbonyl]oxy-3-(methoxymethoxy)-2,5-dimethylhexanoyl]-L-leucyl]-L-prolyl-N,O-dimethyl-L-tyrosyl]-L-threonyl] 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:

(2R,3S,4S)-4-(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-2,5-dimethyl-3-hexanol (126587-67-5) → cyclo-[N-(tert-butyloxycarbonyl)-O-[[N-[(2S,3R,4S)-4-[(1S,2S,3S)-3-amino-2-benzyloxycyclohexanecarbonyl]oxy-3-(methoxymethoxy)-2,5-dimethylhexanoyl]-L-leucyl]-L-prolyl-N,O-dimethyl-L-tyrosyl]-L-threonyl] (339570-96-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

2: 44 percent / LiAlH₄ / diethyl ether / 2 h / -10 °C

3: 98 percent / DIEA / CH₂Cl₂ / 20 °C

4: 89 percent / HCO₂H / Pd / methanol / 0.33 h

5: 47 percent / DMAP; DCC / toluene

6: 94 percent / Amberlyst 15 / methanol / 20 h

7: Dess-Martin reagent / CH₂Cl₂ / 4 h

8: NaClO₂; 5percent NaH₂PO₄ / dimethylsulfoxide; acetonitrile

9: 94.1 mg / DMAP; DCC / CH₂Cl₂

10: Me₃P; H₂O / tetrahydrofuran; toluene / 1 h

11: 95 mg / HATU; collidine / dimethylformamide

12: H₂ / 10percent Pd/C / ethanol / 6 h / 2327.23 - 2585.81 Torr

13: 6.4 mg / HATU; DIEA / dimethylformamide

With 2,3,5-trimethyl-pyridine; dmap; sodium chlorite; lithium aluminium tetrahydride; formic acid; Amberlyst 15; water; hydrogen; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; trimethylphosphane; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 7: Dess-Martin oxidation;

DOI:10.1021/jo001640n

Reference yield:

acetic acid (6S)-(10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decane-4-carbonyl)-(1R)-cyclohex-2-enyl ester (158195-43-8) → cyclo-[N-(tert-butyloxycarbonyl)-O-[[N-[(2S,3R,4S)-4-[(1S,2S,3S)-3-amino-2-benzyloxycyclohexanecarbonyl]oxy-3-(methoxymethoxy)-2,5-dimethylhexanoyl]-L-leucyl]-L-prolyl-N,O-dimethyl-L-tyrosyl]-L-threonyl] (339570-96-6)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 98 percent / LiOH; H₂O / tetrahydrofuran / 48 h / 20 °C

2.1: 70 percent / Ag(collidine)2ClO₄; I₂ / CH₂Cl₂ / 3 h / -20 °C

3.1: 84 percent / tris(trimethylsilyl)silane; AIBN / benzene / 4 h / Heating

4.1: 85 percent / NaHMDS; Bu₄NI / toluene / 12 h / 20 °C

5.1: K₂CO₃ / 36 h

5.2: pyridine / CH₂Cl₂ / 2 h / 0 °C

6.1: 447.8 mg / NaN₃ / dimethylformamide

7.1: 97 percent / LiOH; H₂O / tetrahydrofuran / 48 h / 20 °C

8.1: 47 percent / DMAP; DCC / toluene

9.1: 94 percent / Amberlyst 15 / methanol / 20 h

10.1: Dess-Martin reagent / CH₂Cl₂ / 4 h

11.1: NaClO₂; 5percent NaH₂PO₄ / dimethylsulfoxide; acetonitrile

12.1: 94.1 mg / DMAP; DCC / CH₂Cl₂

13.1: Me₃P; H₂O / tetrahydrofuran; toluene / 1 h

14.1: 95 mg / HATU; collidine / dimethylformamide

15.1: H₂ / 10percent Pd/C / ethanol / 6 h / 2327.23 - 2585.81 Torr

16.1: 6.4 mg / HATU; DIEA / dimethylformamide

With 2,3,5-trimethyl-pyridine; dmap; lithium hydroxide; sodium chlorite; sodium azide; Amberlyst 15; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; Ag(collidine)2ClO₄; water; hydrogen; iodine; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; trimethylphosphane; 10percent Pd/C; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 10.1: Dess-Martin oxidation;

DOI:10.1021/jo001640n

Reference yield:

(1S,2R)-2-hydroxy-3-cyclohexanecarboxylic acid (159517-29-0) → cyclo-[N-(tert-butyloxycarbonyl)-O-[[N-[(2S,3R,4S)-4-[(1S,2S,3S)-3-amino-2-benzyloxycyclohexanecarbonyl]oxy-3-(methoxymethoxy)-2,5-dimethylhexanoyl]-L-leucyl]-L-prolyl-N,O-dimethyl-L-tyrosyl]-L-threonyl] (339570-96-6)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 70 percent / Ag(collidine)2ClO₄; I₂ / CH₂Cl₂ / 3 h / -20 °C

2.1: 84 percent / tris(trimethylsilyl)silane; AIBN / benzene / 4 h / Heating

3.1: 85 percent / NaHMDS; Bu₄NI / toluene / 12 h / 20 °C

4.1: K₂CO₃ / 36 h

4.2: pyridine / CH₂Cl₂ / 2 h / 0 °C

5.1: 447.8 mg / NaN₃ / dimethylformamide

6.1: 97 percent / LiOH; H₂O / tetrahydrofuran / 48 h / 20 °C

7.1: 47 percent / DMAP; DCC / toluene

8.1: 94 percent / Amberlyst 15 / methanol / 20 h

9.1: Dess-Martin reagent / CH₂Cl₂ / 4 h

10.1: NaClO₂; 5percent NaH₂PO₄ / dimethylsulfoxide; acetonitrile

11.1: 94.1 mg / DMAP; DCC / CH₂Cl₂

12.1: Me₃P; H₂O / tetrahydrofuran; toluene / 1 h

13.1: 95 mg / HATU; collidine / dimethylformamide

14.1: H₂ / 10percent Pd/C / ethanol / 6 h / 2327.23 - 2585.81 Torr

15.1: 6.4 mg / HATU; DIEA / dimethylformamide

With 2,3,5-trimethyl-pyridine; dmap; lithium hydroxide; sodium chlorite; sodium azide; Amberlyst 15; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; Ag(collidine)2ClO₄; water; hydrogen; iodine; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; trimethylphosphane; 10percent Pd/C; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 9.1: Dess-Martin oxidation;

DOI:10.1021/jo001640n

upstream raw materials:

(2R,3S,4S)-4-(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-2,5-dimethyl-3-hexanol

acetic acid (6S)-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-(1R)-cyclohex-2-enyl ester

(1R,5S,8S)-8-hydroxy-7-oxa-bicyclo[3.2.1]-octan-6-one

(1S,2R)-2-hydroxy-3-cyclohexanecarboxylic acid

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