(-)-(1R,5R,6R,7S,7aR)-1-[2-(4-methoxyphenyl)methoxy]ethyl-5-(phenylmethoxy)methyl-5,6,7,7a-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one

Base Information

Chemical Name:(-)-(1R,5R,6R,7S,7aR)-1-[2-(4-methoxyphenyl)methoxy]ethyl-5-(phenylmethoxy)methyl-5,6,7,7a-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one
CAS No.:618384-55-7
Molecular Formula:C₂₄H₂₉NO₇
Molecular Weight:443.497
Hs Code.:

Synonyms:(-)-(1R,5R,6R,7S,7aR)-1-[2-(4-methoxyphenyl)methoxy]ethyl-5-(phenylmethoxy)methyl-5,6,7,7a-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one

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Chemical Property of (-)-(1R,5R,6R,7S,7aR)-1-[2-(4-methoxyphenyl)methoxy]ethyl-5-(phenylmethoxy)methyl-5,6,7,7a-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one

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Technology Process of (-)-(1R,5R,6R,7S,7aR)-1-[2-(4-methoxyphenyl)methoxy]ethyl-5-(phenylmethoxy)methyl-5,6,7,7a-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one

There total 10 articles about (-)-(1R,5R,6R,7S,7aR)-1-[2-(4-methoxyphenyl)methoxy]ethyl-5-(phenylmethoxy)methyl-5,6,7,7a-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one 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: 82.0%

: 618384-50-2
(+)-4S-ethenyl-5R-[2-(4-methoxyphenyl)methoxy]ethyl-3-(1S-phenylmethoxymethyl-2-propenyl)-1,3-oxazolidin-2-one

: 618384-55-7
(-)-(1R,5R,6R,7S,7aR)-1-[2-(4-methoxyphenyl)methoxy]ethyl-5-(phenylmethoxy)methyl-5,6,7,7a-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one

Guidance literature:: With potassium osmate(VI); 4-methylmorpholine N-oxide; In water; acetone; at 20 ℃; for 24h;
DOI:10.1021/jo034914q

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 618384-55-7
(-)-(1R,5R,6R,7S,7aR)-1-[2-(4-methoxyphenyl)methoxy]ethyl-5-(phenylmethoxy)methyl-5,6,7,7a-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one

Guidance literature:: Multi-step reaction with 9 steps

1: 93 percent / NaH / tetrahydrofuran / 22 h

2: 79 percent / n-BuLi / tetrahydrofuran; hexane / 20 h / 20 °C

3: 89 percent / Red-Al / tetrahydrofuran; toluene / 4 h / 20 °C

4: T-BuOOH; CaH₂; D-(-)-diisopropyl tartrate / silica gel; Ti(O-i-Pr)4 / CH₂Cl₂ / 24 h / -20 °C

5: Et₃N; DMSO; (COCl)2 / CH₂Cl₂ / 0.42 h / -60 - 20 °C

6: 1.51 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 2 h / -10 °C

7: 98 percent / lithium triflate / acetonitrile / 72 h / 120 °C

8: 79 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

9: 82 percent / 4-morpholine N-oxide; K₂OsO₄*2H₂O / acetone; H₂O / 24 h / 20 °C

With tert.-butylhydroperoxide; potassium osmate(VI); n-butyllithium; calcium hydride; oxalyl dichloride; potassium hexamethylsilazane; sodium hydride; lithium trifluoromethanesulfonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; titanium(IV) isopropylate; silica gel; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene; acetonitrile; 5: Swern oxidation / 6: Wittig olefination;
DOI:10.1021/jo034914q

Reference yield:

: 146916-76-9
5-(4-methoxyphenyl)methoxy-2-pentyn-1-ol

: 618384-55-7
(-)-(1R,5R,6R,7S,7aR)-1-[2-(4-methoxyphenyl)methoxy]ethyl-5-(phenylmethoxy)methyl-5,6,7,7a-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / Red-Al / tetrahydrofuran; toluene / 4 h / 20 °C

2: T-BuOOH; CaH₂; D-(-)-diisopropyl tartrate / silica gel; Ti(O-i-Pr)4 / CH₂Cl₂ / 24 h / -20 °C

3: Et₃N; DMSO; (COCl)2 / CH₂Cl₂ / 0.42 h / -60 - 20 °C

4: 1.51 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 2 h / -10 °C

5: 98 percent / lithium triflate / acetonitrile / 72 h / 120 °C

6: 79 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

7: 82 percent / 4-morpholine N-oxide; K₂OsO₄*2H₂O / acetone; H₂O / 24 h / 20 °C

With tert.-butylhydroperoxide; potassium osmate(VI); calcium hydride; oxalyl dichloride; potassium hexamethylsilazane; lithium trifluoromethanesulfonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; titanium(IV) isopropylate; silica gel; In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile; 3: Swern oxidation / 4: Wittig olefination;
DOI:10.1021/jo034914q