(R)-2-[(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-3-methyl-tetrahydro-pyran-2-yl]-propionaldehyde

Base Information

• Chemical Name: (R)-2-[(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-3-methyl-tetrahydro-pyran-2-yl]-propionaldehyde
• CAS No.: 126394-31-8
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456

Synonyms:(R)-2-[(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-3-methyl-tetrahydro-pyran-2-yl]-propionaldehyde

Chemical Property of (R)-2-[(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-3-methyl-tetrahydro-pyran-2-yl]-propionaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (R)-2-[(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-3-methyl-tetrahydro-pyran-2-yl]-propionaldehyde

There total 19 articles about (R)-2-[(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-3-methyl-tetrahydro-pyran-2-yl]-propionaldehyde 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:

(2S,3R,4S)-1-benzyloxy-3,5-isopropylidenedioxy-2,4-dimethylpentane (81470-77-1,98102-72-8,100760-30-3,115181-74-3,133006-91-4,135211-99-3,138124-14-8,145514-09-6) → (R)-2-[(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-3-methyl-tetrahydro-pyran-2-yl]-propionaldehyde (126394-31-8)

Guidance literature:

Multi-step reaction with 15 steps

1: 96 percent / hydrogen / 10percent Pd/C / ethanol / 3.5 h / Ambient temperature

2: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 30 min, 2) CH₂Cl₂, -70 to 0 deg C

3: 1) NaH / 1) DMF, 45 min, 0 deg C, 2) DMF, THF, 0 to 20 deg C

4: 94 percent / hydrogen / 10percent Pd/C / ethyl acetate

5: 97 percent / tetrahydrofuran / 3 h / -40 °C

6: 1) O₃, 2) NaBH₄ / 1) CH₂Cl₂, -78 deg C, 20 min, 2) CH₂Cl₂, MeOH, -78 deg C, 15 min

7: 94 percent / Et₃N / toluene / 2 h / 0 °C

8: 1N HCl / tetrahydrofuran / 4 h / Ambient temperature

9: K₂CO₃ / methanol; H₂O / 1 h

10: 91 percent / NaH / dimethylsulfoxide / 1 h / Ambient temperature

11: 83 percent / CSA / CH₂Cl₂ / 0.33 h / 0 °C

12: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

13: 28 percent / (Ph₃P)3RhCl / acetonitrile / 9 h / 160 °C / sealed tube

14: 100 percent / DDQ / CH₂Cl₂; H₂O

15: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

With hydrogenchloride; sodium tetrahydroborate; Wilkinson's catalyst; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; sodium hydride; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile;

DOI:10.1248/cpb.37.1698

Reference yield:

(2S,3S,4S)-5-Benzyloxy-2,4-dimethylpentan-1,3-diol (81520-10-7) → (R)-2-[(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-3-methyl-tetrahydro-pyran-2-yl]-propionaldehyde (126394-31-8)

Guidance literature:

Multi-step reaction with 16 steps

1: CSA / acetone / 0.5 h / Ambient temperature

2: 96 percent / hydrogen / 10percent Pd/C / ethanol / 3.5 h / Ambient temperature

3: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 30 min, 2) CH₂Cl₂, -70 to 0 deg C

4: 1) NaH / 1) DMF, 45 min, 0 deg C, 2) DMF, THF, 0 to 20 deg C

5: 94 percent / hydrogen / 10percent Pd/C / ethyl acetate

6: 97 percent / tetrahydrofuran / 3 h / -40 °C

7: 1) O₃, 2) NaBH₄ / 1) CH₂Cl₂, -78 deg C, 20 min, 2) CH₂Cl₂, MeOH, -78 deg C, 15 min

8: 94 percent / Et₃N / toluene / 2 h / 0 °C

9: 1N HCl / tetrahydrofuran / 4 h / Ambient temperature

10: K₂CO₃ / methanol; H₂O / 1 h

11: 91 percent / NaH / dimethylsulfoxide / 1 h / Ambient temperature

12: 83 percent / CSA / CH₂Cl₂ / 0.33 h / 0 °C

13: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

14: 28 percent / (Ph₃P)3RhCl / acetonitrile / 9 h / 160 °C / sealed tube

15: 100 percent / DDQ / CH₂Cl₂; H₂O

16: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

With hydrogenchloride; sodium tetrahydroborate; Wilkinson's catalyst; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; sodium hydride; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetone; toluene; acetonitrile;

DOI:10.1248/cpb.37.1698

Reference yield:

5-O-benzyl-2,4-dideoxy-3-O-formyl-2,4-di-C-methyl-L-lyxose (108470-05-9) → (R)-2-[(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-3-methyl-tetrahydro-pyran-2-yl]-propionaldehyde (126394-31-8)

Guidance literature:

Multi-step reaction with 17 steps

1: LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

2: CSA / acetone / 0.5 h / Ambient temperature

3: 96 percent / hydrogen / 10percent Pd/C / ethanol / 3.5 h / Ambient temperature

4: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 30 min, 2) CH₂Cl₂, -70 to 0 deg C

5: 1) NaH / 1) DMF, 45 min, 0 deg C, 2) DMF, THF, 0 to 20 deg C

6: 94 percent / hydrogen / 10percent Pd/C / ethyl acetate

7: 97 percent / tetrahydrofuran / 3 h / -40 °C

8: 1) O₃, 2) NaBH₄ / 1) CH₂Cl₂, -78 deg C, 20 min, 2) CH₂Cl₂, MeOH, -78 deg C, 15 min

9: 94 percent / Et₃N / toluene / 2 h / 0 °C

10: 1N HCl / tetrahydrofuran / 4 h / Ambient temperature

11: K₂CO₃ / methanol; H₂O / 1 h

12: 91 percent / NaH / dimethylsulfoxide / 1 h / Ambient temperature

13: 83 percent / CSA / CH₂Cl₂ / 0.33 h / 0 °C

14: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

15: 28 percent / (Ph₃P)3RhCl / acetonitrile / 9 h / 160 °C / sealed tube

16: 100 percent / DDQ / CH₂Cl₂; H₂O

17: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

With hydrogenchloride; sodium tetrahydroborate; Wilkinson's catalyst; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; sodium hydride; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetone; toluene; acetonitrile;

DOI:10.1248/cpb.37.1698

upstream raw materials:

(S)-2-<(2R,3S,6R)-6-<(S)-1-(benzyloxymethyl)propyl>-3-methyltetrahydropyran-2-yl>propan-1-ol

(2S,3S,4S)-5-Benzyloxy-2,4-dimethylpentan-1,3-diol

(2S,3R,4S)-1-benzyloxy-3,5-isopropylidenedioxy-2,4-dimethylpentane

(2S,3R,4S)-6-[(S)-2-((S)-1-Benzyloxymethyl-propyl)-oxiranyl]-2,4-dimethyl-hexane-1,3-diol

Downstream raw materials:

(2R,3S,6R)-6-((S)-1-Benzyloxymethyl-propyl)-2-((R)-1-[1,3]dioxolan-2-yl-ethyl)-3-methyl-tetrahydro-pyran

salinomycin

C₅₈H₈₆O₁₃

C₅₇H₈₄O₁₂

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