(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

Base Information

Chemical Name:(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
CAS No.:566202-80-0
Molecular Formula:C₅₉H₆₆N₂O₁₁Si
Molecular Weight:1007.27
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 21 articles about (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 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: 66.0%

: 91174-01-5
sodium [(benzyloxy)carbonyl]chloroamide

: 566202-79-7
(2'R,3'R)-3-[3'-{(3''-acetoxypropyl)-[4''-(tert-butyldiphenylsilanyloxy)butyl]carbamoyl}-2'-(4''-benzyloxyphenyl)-2',3'-dihydrobenzofuran-5'-yl]acrylic acid methyl ester

: 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

Guidance literature:: With potassium dioxotetrahydroxoosmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine; In propan-1-ol; water; at 20 ℃; for 4h;
DOI:10.1016/j.tet.2004.06.144

Reference yield:

: 621-84-1
O-benzyl carbamate

: 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

Guidance literature:: Multi-step reaction with 2 steps

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

2: 66 percent / (DHQD)2PHAL; K₂OsO₂(OH)4 / propan-1-ol; H₂O / 4 h / 20 °C

With sodium hydroxide; potassium dioxotetrahydroxoosmate(VI); tert-butylhypochlorite; 1,4-bis(9-O-dihydroquinidine)phthalazine; In propan-1-ol; water; 2: Sharpless aminohydroxylation;
DOI:10.1016/j.tet.2004.06.144

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 6 steps

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

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

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

4: 88 percent / pyridine / 0 - 20 °C

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

6: 66 percent / (DHQD)2PHAL; K₂OsO₂(OH)4 / propan-1-ol; H₂O / 4 h / 20 °C

With pyridine; palladium diacetate; potassium dioxotetrahydroxoosmate(VI); dimethylaluminum chloride; potassium carbonate; thiophenol; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; tris-(o-tolyl)phosphine; diethylazodicarboxylate; In tetrahydrofuran; propan-1-ol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Mitsunobu reaction / 5: Heck reaction / 6: Sharpless aminohydroxylation;
DOI:10.1016/j.tet.2004.06.144