(2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-carbaldehyde

Base Information

Chemical Name:(2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-carbaldehyde
CAS No.:862603-26-7
Molecular Formula:C₁₇H₂₂O₄
Molecular Weight:290.359
Hs Code.:

Synonyms:(2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-carbaldehyde

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Chemical Property of (2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-carbaldehyde

Chemical Property:

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Technology Process of (2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-carbaldehyde

There total 27 articles about (2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-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:

: 170305-54-1
(2S,5R)-5-<(Benzyloxy)methyl>tetrahydrofuran-2-carboxaldehyde

: 862603-26-7
(2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-carbaldehyde

Guidance literature:: Multi-step reaction with 9 steps

1.1: 96 percent / MgBr₂*Et₂O

2.1: aq. OsO₄; 4-methylmorpholine N-oxide / acetone / 1.5 h / 20 °C

3.1: aq. NaIO₄ / ethanol / 1 h / 20 °C

4.1: 1.467 g / NaBH₄ / H₂O; ethanol / 0.5 h

5.1: 90 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

6.1: 80 percent / N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

7.1: 93 percent / NaI / acetone / 9 h / Heating

8.1: 95 percent / N-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -20 °C

9.1: pyridine; trifluoroacetic anhydride / acetonitrile / 0.33 h / 0 °C

9.2: 78 percent / aq. KOAc / acetonitrile / 1.33 h / 0 °C

With 4-methyl-morpholine; pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; triethyl borane; tri-n-butyl-tin hydride; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic anhydride; sodium iodide; magnesium bromide; In ethanol; hexane; dichloromethane; water; acetone; toluene; acetonitrile; 9.1: Pummerer rearrangement;
DOI:10.1021/ja0526867

Reference yield:

: (R)-4-Benzyloxymethyl-2-phenyl-[1,3]dioxane

: 862603-26-7
(2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-carbaldehyde

Guidance literature:: Multi-step reaction with 15 steps

1.1: aq. AcOH

1.2: NaIO₄

2.1: Et₃N

3.1: N-methylmorpholine

4.1: NaI

5.1: 95 percent / N-Bu₃SnH; Et₃B

6.1: trifluoroacetic anhydride; pyridine

6.2: 84 percent / KOAc

7.1: 96 percent / MgBr₂*Et₂O

8.1: aq. OsO₄; 4-methylmorpholine N-oxide / acetone / 1.5 h / 20 °C

9.1: aq. NaIO₄ / ethanol / 1 h / 20 °C

10.1: 1.467 g / NaBH₄ / H₂O; ethanol / 0.5 h

11.1: 90 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

12.1: 80 percent / N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

13.1: 93 percent / NaI / acetone / 9 h / Heating

14.1: 95 percent / N-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -20 °C

15.1: pyridine; trifluoroacetic anhydride / acetonitrile / 0.33 h / 0 °C

15.2: 78 percent / aq. KOAc / acetonitrile / 1.33 h / 0 °C

With 4-methyl-morpholine; pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; triethyl borane; tri-n-butyl-tin hydride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic anhydride; sodium iodide; magnesium bromide; In ethanol; hexane; dichloromethane; water; acetone; toluene; acetonitrile; 6.1: Pummerer rearrangement / 15.1: Pummerer rearrangement;
DOI:10.1021/ja0526867

Reference yield:

: (S)-3-((2S,5R)-5-Benzyloxymethyl-tetrahydro-furan-2-yl)-3-hydroxy-propionaldehyde

: 862603-26-7
(2S,5R,2'S,5'R)-5'-Benzyloxymethyl-octahydro-[2,2']bifuranyl-5-carbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1.467 g / NaBH₄ / H₂O; ethanol / 0.5 h

2.1: 90 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

3.1: 80 percent / N-methylmorpholine / CH₂Cl₂ / 12 h / 20 °C

4.1: 93 percent / NaI / acetone / 9 h / Heating

5.1: 95 percent / N-Bu₃SnH; Et₃B / toluene; hexane / 0.5 h / -20 °C

6.1: pyridine; trifluoroacetic anhydride / acetonitrile / 0.33 h / 0 °C

6.2: 78 percent / aq. KOAc / acetonitrile / 1.33 h / 0 °C

With 4-methyl-morpholine; pyridine; sodium tetrahydroborate; triethyl borane; tri-n-butyl-tin hydride; triethylamine; trifluoroacetic anhydride; sodium iodide; In ethanol; hexane; dichloromethane; water; acetone; toluene; acetonitrile; 6.1: Pummerer rearrangement;
DOI:10.1021/ja0526867