(2R,3R)-3-[(2R,3R)-3-{(3-Acetoxy-propyl)-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-carbamoyl}-2-(4-benzyloxy-phenyl)-2,3-dihydro-benzofuran-5-yl]-3-benzyloxycarbonylamino-2-chloro-propionic acid methyl ester

Base Information

Chemical Name:(2R,3R)-3-[(2R,3R)-3-{(3-Acetoxy-propyl)-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-carbamoyl}-2-(4-benzyloxy-phenyl)-2,3-dihydro-benzofuran-5-yl]-3-benzyloxycarbonylamino-2-chloro-propionic acid methyl ester
CAS No.:566202-95-7
Molecular Formula:C₅₉H₆₅ClN₂O₁₀Si
Molecular Weight:1025.71
Hs Code.:

(2R,3R)-3-[(2R,3R)-3-{(3-Acetoxy-propyl)-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-carbamoyl}-2-(4-benzyloxy-phenyl)-2,3-dihydro-benzofuran-5-yl]-3-benzyloxycarbonylamino-2-chloro-propionic acid methyl ester

Synonyms:(2R,3R)-3-[(2R,3R)-3-{(3-Acetoxy-propyl)-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-carbamoyl}-2-(4-benzyloxy-phenyl)-2,3-dihydro-benzofuran-5-yl]-3-benzyloxycarbonylamino-2-chloro-propionic acid methyl ester

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Chemical Property of (2R,3R)-3-[(2R,3R)-3-{(3-Acetoxy-propyl)-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-carbamoyl}-2-(4-benzyloxy-phenyl)-2,3-dihydro-benzofuran-5-yl]-3-benzyloxycarbonylamino-2-chloro-propionic acid methyl ester

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Technology Process of (2R,3R)-3-[(2R,3R)-3-{(3-Acetoxy-propyl)-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-carbamoyl}-2-(4-benzyloxy-phenyl)-2,3-dihydro-benzofuran-5-yl]-3-benzyloxycarbonylamino-2-chloro-propionic acid methyl ester

There total 11 articles about (2R,3R)-3-[(2R,3R)-3-{(3-Acetoxy-propyl)-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-carbamoyl}-2-(4-benzyloxy-phenyl)-2,3-dihydro-benzofuran-5-yl]-3-benzyloxycarbonylamino-2-chloro-propionic acid methyl ester 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: 87.0%

: 566202-80-0
(2S,3R,2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]-3-benzyloxycarbonylamino-2-hydroxypropionic acid methyl ester

: 566202-95-7
(2R,3R)-3-[(2R,3R)-3-{(3-Acetoxy-propyl)-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-carbamoyl}-2-(4-benzyloxy-phenyl)-2,3-dihydro-benzofuran-5-yl]-3-benzyloxycarbonylamino-2-chloro-propionic acid methyl ester

Guidance literature:: With tetrachloromethane; triphenylphosphine; In toluene; at 100 ℃; for 2h;
DOI:10.1021/ja036011k

Reference yield:

: 621-84-1
O-benzyl carbamate

: 566202-95-7
(2R,3R)-3-[(2R,3R)-3-{(3-Acetoxy-propyl)-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-carbamoyl}-2-(4-benzyloxy-phenyl)-2,3-dihydro-benzofuran-5-yl]-3-benzyloxycarbonylamino-2-chloro-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: t-butyl hypochlorite; aq. NaOH / propan-1-ol / 0.25 h / 20 °C

2: 10.2 g / (DHQD)2PHAL; aq. K₂OsO₂(OH)4 / propan-1-ol / 4 h

3: 87 percent / PPh₃; CCl₄ / toluene / 2 h / 100 °C

With tetrachloromethane; sodium hydroxide; potassium dioxotetrahydroxoosmate(VI); tert-butylhypochlorite; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; In propan-1-ol; toluene; 2: Sharpless asymmetric aminohydroxylation;
DOI:10.1021/ja036011k

Reference yield:

: 566202-75-3
(2R,3R)-2-(4-benzyloxyphenyl)-5-bromo-2,3-dihydrobenzofuran-3-carboxylic acid

: 566202-95-7
(2R,3R)-3-[(2R,3R)-3-{(3-Acetoxy-propyl)-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-carbamoyl}-2-(4-benzyloxy-phenyl)-2,3-dihydro-benzofuran-5-yl]-3-benzyloxycarbonylamino-2-chloro-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / PPh₃; DEAD / tetrahydrofuran; toluene / 0 - 20 °C

2: 88 percent / K₂CO₃; PhSH / dimethylformamide; acetonitrile / 0.67 h / 50 °C

3: 67 percent / Me₂AlCl / CH₂Cl₂ / 3 h / Heating

4: 88 percent / pyridine / 8 h / 20 °C

5: 84 percent / tris(o-tolyl)phosphine; Pd(OAc)2; Et₃N / dimethylformamide / 24 h / 100 °C

6: 10.2 g / (DHQD)2PHAL; aq. K₂OsO₂(OH)4 / propan-1-ol / 4 h

7: 87 percent / PPh₃; CCl₄ / toluene / 2 h / 100 °C

With pyridine; tetrachloromethane; palladium diacetate; potassium dioxotetrahydroxoosmate(VI); dimethylaluminum chloride; potassium carbonate; thiophenol; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; tris-(o-tolyl)phosphine; diethylazodicarboxylate; In tetrahydrofuran; propan-1-ol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 5: Heck reaction / 6: Sharpless asymmetric aminohydroxylation;
DOI:10.1021/ja036011k