(1S',2R,3S,3R,4S)-N-<1'-(3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3'-methylbutyl>-4-<(benzyloxycarbonyl)amino>-5-(benzyloxycarbonyl)-2,3-dihydroxypentamide

Base Information

Chemical Name:(1S',2R,3S,3R,4S)-N-<1'-(3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3'-methylbutyl>-4-<(benzyloxycarbonyl)amino>-5-(benzyloxycarbonyl)-2,3-dihydroxypentamide
CAS No.:142955-61-1
Molecular Formula:C₃₅H₄₀N₂O₁₀
Molecular Weight:648.71
Hs Code.:

(1S',2R,3S,3R,4S)-N-<1'-(3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3'-methylbutyl>-4-<(benzyloxycarbonyl)amino>-5-(benzyloxycarbonyl)-2,3-dihydroxypentamide

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Chemical Property of (1S',2R,3S,3R,4S)-N-<1'-(3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3'-methylbutyl>-4-<(benzyloxycarbonyl)amino>-5-(benzyloxycarbonyl)-2,3-dihydroxypentamide

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Technology Process of (1S',2R,3S,3R,4S)-N-<1'-(3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3'-methylbutyl>-4-<(benzyloxycarbonyl)amino>-5-(benzyloxycarbonyl)-2,3-dihydroxypentamide

There total 11 articles about (1S',2R,3S,3R,4S)-N-<1'-(3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3'-methylbutyl>-4-<(benzyloxycarbonyl)amino>-5-(benzyloxycarbonyl)-2,3-dihydroxypentamide 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: 40.0%

: 142955-56-4
(1S',3S,4S)-(Z)-N-<1'-(3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3'-methylbutyl>-4-<(benzyloxycarbonyl)amino>-5-(benzyloxycarbonyl)-pent-2-enamide

: 142955-60-0
((2S,3S)-2-{(S)-Hydroxy-[(S)-1-((S)-8-hydroxy-1-oxo-isochroman-3-yl)-3-methyl-butylcarbamoyl]-methyl}-5-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester

: 142955-61-1
(1S',2R,3S,3R,4S)-N-<1'-(3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3'-methylbutyl>-4-<(benzyloxycarbonyl)amino>-5-(benzyloxycarbonyl)-2,3-dihydroxypentamide

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In acetone; tert-butyl alcohol; for 18h; Ambient temperature;
DOI:10.1016/0040-4020(95)00776-5

Reference yield:

: 13139-15-6,53296-34-7
N-tert-butoxycarbonyl-L-leucine

: 142955-61-1
(1S',2R,3S,3R,4S)-N-<1'-(3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3'-methylbutyl>-4-<(benzyloxycarbonyl)amino>-5-(benzyloxycarbonyl)-2,3-dihydroxypentamide

Guidance literature:: Multi-step reaction with 8 steps

1: 91 percent / borane*tetrahydrofuran / tetrahydrofuran / 1 h / Ambient temperature

2: 99 percent / pyridine*sulphur trioxide, triethylamine / dimethylsulfoxide / 0.33 h / Ambient temperature

3: 1.) diisopropylamine, n-butyl lithium, 2.) magnesium bromide etherate / 1.) THF/hexane, -78 deg C, 15 min, 2.) THF/hexane, -78 deg C, 15 min, 3.) THF/hexane, -78 deg C, 30 min

4: 1.) potassium hydroxide, 2.) triethylamine, methanesulphonyl chloride, 3.) 2 M aq. NaOH / 1.) ethanol/water, reflux, 3 h, 2.) THF, 0 deg C, 1 h, 3.) water, reflux, 1 h

5: 58 percent / iodine, magnesium / benzene / 1 h / Heating

6: 99 percent / 3 M HCl / methanol / 4 h / 0 °C

7: 75 percent / dicyclohexylcarbodiimide, 1-hydroxy-benzotriazole / dimethylformamide / 18 h / Ambient temperature

8: 40 percent / osmium tetroxide, N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; acetone / 18 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium hydroxide; osmium(VIII) oxide; n-butyllithium; borane-THF; iodine; sulfur trioxide pyridine complex; benzotriazol-1-ol; magnesium bromide ethyl etherate; magnesium; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;
DOI:10.1016/0040-4020(95)00776-5

Reference yield:

: 82010-31-9
(S)-(1-hydroxymethyl-3-methylbutyl)carbamic acid tert-butyl ester

: 142955-61-1
(1S',2R,3S,3R,4S)-N-<1'-(3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3'-methylbutyl>-4-<(benzyloxycarbonyl)amino>-5-(benzyloxycarbonyl)-2,3-dihydroxypentamide

Guidance literature:: Multi-step reaction with 7 steps

1: 99 percent / pyridine*sulphur trioxide, triethylamine / dimethylsulfoxide / 0.33 h / Ambient temperature

2: 1.) diisopropylamine, n-butyl lithium, 2.) magnesium bromide etherate / 1.) THF/hexane, -78 deg C, 15 min, 2.) THF/hexane, -78 deg C, 15 min, 3.) THF/hexane, -78 deg C, 30 min

3: 1.) potassium hydroxide, 2.) triethylamine, methanesulphonyl chloride, 3.) 2 M aq. NaOH / 1.) ethanol/water, reflux, 3 h, 2.) THF, 0 deg C, 1 h, 3.) water, reflux, 1 h

4: 58 percent / iodine, magnesium / benzene / 1 h / Heating

5: 99 percent / 3 M HCl / methanol / 4 h / 0 °C

6: 75 percent / dicyclohexylcarbodiimide, 1-hydroxy-benzotriazole / dimethylformamide / 18 h / Ambient temperature

7: 40 percent / osmium tetroxide, N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; acetone / 18 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium hydroxide; osmium(VIII) oxide; n-butyllithium; iodine; sulfur trioxide pyridine complex; benzotriazol-1-ol; magnesium bromide ethyl etherate; magnesium; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; dicyclohexyl-carbodiimide; In methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;
DOI:10.1016/0040-4020(95)00776-5