(5R,10aR)-6,8-bis(benzyloxy)-5-<<4-(benzyloyx)phenyl>methyl>-9-mercapto-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

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Chemical Name:(5R,10aR)-6,8-bis(benzyloxy)-5-<<4-(benzyloyx)phenyl>methyl>-9-mercapto-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one
CAS No.:228997-26-0
Molecular Formula:C₃₉H₃₅NO₅S
Molecular Weight:629.777
Hs Code.:

Synonyms:(5R,10aR)-6,8-bis(benzyloxy)-5-<<4-(benzyloyx)phenyl>methyl>-9-mercapto-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

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Chemical Property of (5R,10aR)-6,8-bis(benzyloxy)-5-<<4-(benzyloyx)phenyl>methyl>-9-mercapto-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

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Technology Process of (5R,10aR)-6,8-bis(benzyloxy)-5-<<4-(benzyloyx)phenyl>methyl>-9-mercapto-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

There total 19 articles about (5R,10aR)-6,8-bis(benzyloxy)-5-<<4-(benzyloyx)phenyl>methyl>-9-mercapto-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-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:

: 99-10-5
3,5-Dihydroxybenzoic acid

: 228997-26-0
(5R,10aR)-6,8-bis(benzyloxy)-5-<<4-(benzyloyx)phenyl>methyl>-9-mercapto-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

Guidance literature:: Multi-step reaction with 15 steps

1: 1.) NaH / 1) DMF, 1.3 h; 2) DMF, rt, 27 h

2: aq. NaOH / methanol / 3 h / Ambient temperature

3: 90 percent / (EtO)2P(O)CN, Et₃N / dimethylformamide / 2 h

4: 1.) sec-BuLi, TMEDA, 2.) sulfur / 1) THF, cyclohexane, -78 deg C, 1 h; 2) THF, cyclohexane, 0 deg C, 1.5 h; 3) THF, cyclohexane, 0 deg C, 2 h

5: 87 percent / aq. HCl / methanol / 2.5 h / 60 - 64 °C

6: 1.) NaH / 1) DMF, rt, 1 h; 2) DMF, 0 deg C, 10 min, rt, 4.5 h

7: 97 percent / LiAlH₄ / tetrahydrofuran / 1) 0 deg C, 35 min; 2) reflux, 3 h

8: 80 percent / ethyl chloroformate / benzene / 23 h / Ambient temperature

9: 1.) diisopropylamine, BuLi / 1) THF, hexane, -78 deg C, 20 min; 2) THF, hexane, -78 deg C, 2 h, -50 deg C, 18 h

10: 79 percent / aq. HCl / methanol / 9 h / Ambient temperature

11: 94 percent / Na₂CO₃ / benzene; H₂O / 1 h / 8 - 10 °C

12: 1.) hexamethyldisiloxane, P₂O₅, 2.) NaBH₄ / 1) CHCl₃, reflux, 10 h; 2) MeOH, -78 deg C, 1 h

13: 87 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

14: 95 percent / NaOEt / ethanol / 23 h / Heating

15: 1.) mercuric trifluoroacetate, anisole, 2.) NaBH₄ / 1) EtOH, rt, 19 h; 2) EtOH, 0 deg C, 15 min

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Hexamethyldisiloxane; diethyl cyanophosphonate; sec.-butyllithium; sodium ethanolate; mercury(II) trifluoroacetate; phosphorus pentoxide; chloroformic acid ethyl ester; sodium hydride; sodium carbonate; sulfur; methoxybenzene; triethylamine; diisopropylamine; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4020(99)00199-4

Reference yield:

: 39188-62-0
2-(4-(benzyloxy)phenyl)acetyl chloride

: 228997-26-0
(5R,10aR)-6,8-bis(benzyloxy)-5-<<4-(benzyloyx)phenyl>methyl>-9-mercapto-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / Na₂CO₃ / benzene; H₂O / 1 h / 8 - 10 °C

2: 1.) hexamethyldisiloxane, P₂O₅, 2.) NaBH₄ / 1) CHCl₃, reflux, 10 h; 2) MeOH, -78 deg C, 1 h

3: 87 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

4: 95 percent / NaOEt / ethanol / 23 h / Heating

5: 1.) mercuric trifluoroacetate, anisole, 2.) NaBH₄ / 1) EtOH, rt, 19 h; 2) EtOH, 0 deg C, 15 min

With sodium tetrahydroborate; lithium aluminium tetrahydride; Hexamethyldisiloxane; sodium ethanolate; mercury(II) trifluoroacetate; phosphorus pentoxide; sodium carbonate; methoxybenzene; In tetrahydrofuran; ethanol; water; benzene;
DOI:10.1016/S0040-4020(99)00199-4

Reference yield:

: 6547-53-1
2-[4-(benzyloxy)benzyl]acetic acid

: 228997-26-0
(5R,10aR)-6,8-bis(benzyloxy)-5-<<4-(benzyloyx)phenyl>methyl>-9-mercapto-1,5,10,10a-tetrahydroxazolo<3,4-b>isoquinolin-3(3H)-one

Guidance literature:: Multi-step reaction with 6 steps

1: PCl₅ / hexane / 0.5 h / Heating

2: 94 percent / Na₂CO₃ / benzene; H₂O / 1 h / 8 - 10 °C

3: 1.) hexamethyldisiloxane, P₂O₅, 2.) NaBH₄ / 1) CHCl₃, reflux, 10 h; 2) MeOH, -78 deg C, 1 h

4: 87 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

5: 95 percent / NaOEt / ethanol / 23 h / Heating

6: 1.) mercuric trifluoroacetate, anisole, 2.) NaBH₄ / 1) EtOH, rt, 19 h; 2) EtOH, 0 deg C, 15 min

With sodium tetrahydroborate; lithium aluminium tetrahydride; Hexamethyldisiloxane; phosphorus pentachloride; sodium ethanolate; mercury(II) trifluoroacetate; phosphorus pentoxide; sodium carbonate; methoxybenzene; In tetrahydrofuran; ethanol; hexane; water; benzene;
DOI:10.1016/S0040-4020(99)00199-4