(2R,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-chloropropionic acid methyl ester

Base Information

Chemical Name:(2R,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-chloropropionic acid methyl ester
CAS No.:795296-97-8
Molecular Formula:C₅₉H₆₅ClN₂O₁₀Si
Molecular Weight:1025.71
Hs Code.:

(2R,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-chloropropionic acid methyl ester

Synonyms:(2R,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-chloropropionic acid methyl ester

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Chemical Property of (2R,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-chloropropionic acid methyl ester

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Technology Process of (2R,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-chloropropionic acid methyl ester

There total 17 articles about (2R,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-chloropropionic 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

: 795296-97-8
(2R,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-chloropropionic acid methyl ester

Guidance literature:: With tetrachloromethane; triphenylphosphine; In toluene; at 100 ℃; for 2h;
DOI:10.1016/j.tet.2004.06.144

Reference yield:

: 621-84-1
O-benzyl carbamate

: 795296-97-8
(2R,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-chloropropionic acid methyl ester

Guidance literature:: Multi-step reaction with 3 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

3: 87 percent / CCl₄; PPh₃ / 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; water; toluene; 2: Sharpless aminohydroxylation;
DOI:10.1016/j.tet.2004.06.144

Reference yield:

: 4397-53-9
p-benzyloxybenzaldehyde

: 795296-97-8
(2R,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-chloropropionic acid methyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: 99 percent / NaBH₄ / tetrahydrofuran; H₂O

2.1: 98 percent / SOCl₂

3.1: 95 percent / K₂CO₃ / dimethylformamide / 4 h / 60 °C

4.1: O₃ / CH₂Cl₂; methanol / 7.5 h / -78 °C

4.2: Me₂S / CH₂Cl₂; methanol / -78 - 20 °C

5.1: 137 g / 2-methyl-2-butene; NaH₂PO₄*2H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 84 h / 20 °C

6.1: 80 percent / diethyl azodicarboxylate; PPh₃ / toluene / 0 - 20 °C

7.1: p-acetamidobenzenesulfonyl azide; DBU / acetonitrile / 0 - 20 °C

8.1: 5.10 g / Rh₂(S-DOSP)4 / CH₂Cl₂ / 0.5 h / 0 °C

9.1: 90 percent / Ba(OH)2*8H₂O / tetrahydrofuran; methanol / 0 - 20 °C

10.1: 96 percent / diethyl azodicarboxylate; PPh₃ / tetrahydrofuran; toluene / 0 - 20 °C

11.1: 88 percent / PhSH; K₂CO₃ / dimethylformamide; acetonitrile / 0.67 h / 50 °C

12.1: 67 percent / Me₂AlCl / CH₂Cl₂ / 3 h / Heating

13.1: 88 percent / pyridine / 0 - 20 °C

14.1: 84 percent / Pd(OAc)2; tris(o-tolyl)phosphine / dimethylformamide / 24 h / 100 °C

15.1: 66 percent / (DHQD)2PHAL; K₂OsO₂(OH)4 / propan-1-ol; H₂O / 4 h / 20 °C

16.1: 87 percent / CCl₄; PPh₃ / toluene / 2 h / 100 °C

With pyridine; tetrachloromethane; palladium diacetate; barium dihydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; thionyl chloride; 2-methyl-but-2-ene; potassium dioxotetrahydroxoosmate(VI); Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4; 4-acetamidobenzenesulfonyl azide; dimethylaluminum chloride; potassium carbonate; ozone; thiophenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; tris-(o-tolyl)phosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 6.1: Mitsunobu reaction / 10.1: Mitsunobu reaction / 14.1: Heck reaction / 15.1: Sharpless aminohydroxylation;
DOI:10.1016/j.tet.2004.06.144