(5R,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carbaldehyde

Base Information

Chemical Name:(5R,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carbaldehyde
CAS No.:186819-80-7
Molecular Formula:C₁₅H₁₇NO₄
Molecular Weight:275.304
Hs Code.:

Synonyms:(5R,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carbaldehyde

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Chemical Property of (5R,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carbaldehyde

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Technology Process of (5R,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carbaldehyde

There total 10 articles about (5R,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carbaldehyde 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:

: 186819-71-6
6-Methoxymethoxy-hex-4-yn-1-ol

: 186819-80-7
(5R,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carbaldehyde

Guidance literature:: Multi-step reaction with 10 steps

1: 84 percent / H₂ / Lindlar catalyst / ethyl acetate

2: 81 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

3: 88 percent / CH₂Cl₂

4: 94 percent / DIBALH / tetrahydrofuran

5: 80 percent / Ti(i-PrO)4, L-DIPT, t-BuOOH / CH₂Cl₂ / -23 °C

6: 2.) K₂CO₃, (C₈H₁₇)3NMeCl / 1.) THF, room temperature, 2.) MeCN

7: 1.) conc. HCl, 2.) MsCl, DMAP / 1.) MeOH, 60 deg C, 2.) CH₂Cl₂, room temperature

8: 72 percent / AgOCOCF₃, NaH / tetrahydrofuran / Ambient temperature

9: 93 percent / NaH, Bu₄BI / tetrahydrofuran

10: 1.) OsO₄, NMO, 2.) aq. NaIO₄ / 1.) 1,4-dioxane

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; L-(+)-diisopropyl tartrate; (C₈H₁₇)3NMeCl; hydrogen; silver trifluoroacetate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1021/jo961951r

Reference yield:

: 186819-84-1
(Z)-6-Methoxymethoxy-hex-4-enal

: 186819-80-7
(5R,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / CH₂Cl₂

2: 94 percent / DIBALH / tetrahydrofuran

3: 80 percent / Ti(i-PrO)4, L-DIPT, t-BuOOH / CH₂Cl₂ / -23 °C

4: 2.) K₂CO₃, (C₈H₁₇)3NMeCl / 1.) THF, room temperature, 2.) MeCN

5: 1.) conc. HCl, 2.) MsCl, DMAP / 1.) MeOH, 60 deg C, 2.) CH₂Cl₂, room temperature

6: 72 percent / AgOCOCF₃, NaH / tetrahydrofuran / Ambient temperature

7: 93 percent / NaH, Bu₄BI / tetrahydrofuran

8: 1.) OsO₄, NMO, 2.) aq. NaIO₄ / 1.) 1,4-dioxane

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; L-(+)-diisopropyl tartrate; (C₈H₁₇)3NMeCl; silver trifluoroacetate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; methanesulfonyl chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo961951r

Reference yield:

: 186819-72-7
(2E,6Z)-8-Methoxymethoxy-octa-2,6-dien-1-ol

: 186819-80-7
(5R,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / Ti(i-PrO)4, L-DIPT, t-BuOOH / CH₂Cl₂ / -23 °C

2: 2.) K₂CO₃, (C₈H₁₇)3NMeCl / 1.) THF, room temperature, 2.) MeCN

3: 1.) conc. HCl, 2.) MsCl, DMAP / 1.) MeOH, 60 deg C, 2.) CH₂Cl₂, room temperature

4: 72 percent / AgOCOCF₃, NaH / tetrahydrofuran / Ambient temperature

5: 93 percent / NaH, Bu₄BI / tetrahydrofuran

6: 1.) OsO₄, NMO, 2.) aq. NaIO₄ / 1.) 1,4-dioxane

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; L-(+)-diisopropyl tartrate; (C₈H₁₇)3NMeCl; silver trifluoroacetate; sodium hydride; potassium carbonate; methanesulfonyl chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo961951r