(S)-1-((4R,5S,7R,8S,10R)-7-Benzyloxymethyl-8-methoxy-2,2,10-trimethyl-1,3,6-trioxa-spiro[4.5]decane-4-carbonyl)-piperidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (S)-1-((4R,5S,7R,8S,10R)-7-Benzyloxymethyl-8-methoxy-2,2,10-trimethyl-1,3,6-trioxa-spiro[4.5]decane-4-carbonyl)-piperidine-2-carboxylic acid methyl ester
• CAS No.: 123492-32-0
• Molecular Formula: C₂₇H₃₉NO₈
• Molecular Weight: 505.609

Synonyms:

Chemical Property of (S)-1-((4R,5S,7R,8S,10R)-7-Benzyloxymethyl-8-methoxy-2,2,10-trimethyl-1,3,6-trioxa-spiro[4.5]decane-4-carbonyl)-piperidine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((4R,5S,7R,8S,10R)-7-Benzyloxymethyl-8-methoxy-2,2,10-trimethyl-1,3,6-trioxa-spiro[4.5]decane-4-carbonyl)-piperidine-2-carboxylic acid methyl ester

There total 15 articles about (S)-1-((4R,5S,7R,8S,10R)-7-Benzyloxymethyl-8-methoxy-2,2,10-trimethyl-1,3,6-trioxa-spiro[4.5]decane-4-carbonyl)-piperidine-2-carboxylic acid methyl ester 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:

Methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside (101978-79-4) → (S)-1-((4R,5S,7R,8S,10R)-7-Benzyloxymethyl-8-methoxy-2,2,10-trimethyl-1,3,6-trioxa-spiro[4.5]decane-4-carbonyl)-piperidine-2-carboxylic acid methyl ester (123492-32-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) n-BuLi / 1,2-dimethoxy-ethane; various solvent(s) / 1.) 0 deg C, 2.) room temp., 4h

2: 4 h / Ambient temperature

3: Li, EtNH₂ / tetrahydrofuran; ethanol / 1 h / 10 °C

4: 1.) NaH / 1.) THF, 0 deg C 2.) 36 h

5: 1.) NaH / THF, room temp., 8h

6: AcOH, H₂SO₄ / H₂O / 1.5 h / 90 °C

7: Ac₂O, DMSO / 24 h / Ambient temperature

8: 1.) LDA / THF, -78 deg C, 3h

9: PPTs, H₂O / tetrahydrofuran / 5 h / 55 °C

10: P₂O₅ / 15 h / Ambient temperature

11: LiOH / methanol; H₂O / 6 h / Ambient temperature

12: SOCl₂ / pyridine / 0.17 h / Ambient temperature

13: Et₃N / 2 h / Ambient temperature

With lithium hydroxide; n-butyllithium; thionyl chloride; sulfuric acid; water; phosphorus pentoxide; pyridinium p-toluenesulfonate; acetic anhydride; lithium; sodium hydride; ethylamine; acetic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; 1,2-dimethoxyethane; ethanol; water;

DOI:10.1016/S0040-4039(00)95278-X

Reference yield:

(2R,3S,5R,6S)-2-Hydroxymethyl-6-methoxy-5-methyl-tetrahydro-pyran-3-ol (123474-66-8) → (S)-1-((4R,5S,7R,8S,10R)-7-Benzyloxymethyl-8-methoxy-2,2,10-trimethyl-1,3,6-trioxa-spiro[4.5]decane-4-carbonyl)-piperidine-2-carboxylic acid methyl ester (123492-32-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) NaH / 1.) THF, 0 deg C 2.) 36 h

2: 1.) NaH / THF, room temp., 8h

3: AcOH, H₂SO₄ / H₂O / 1.5 h / 90 °C

4: Ac₂O, DMSO / 24 h / Ambient temperature

5: 1.) LDA / THF, -78 deg C, 3h

6: PPTs, H₂O / tetrahydrofuran / 5 h / 55 °C

7: P₂O₅ / 15 h / Ambient temperature

8: LiOH / methanol; H₂O / 6 h / Ambient temperature

9: SOCl₂ / pyridine / 0.17 h / Ambient temperature

10: Et₃N / 2 h / Ambient temperature

With lithium hydroxide; thionyl chloride; sulfuric acid; water; phosphorus pentoxide; pyridinium p-toluenesulfonate; acetic anhydride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; water;

DOI:10.1016/S0040-4039(00)95278-X

Reference yield:

benzyl bromide (100-39-0) → (S)-1-((4R,5S,7R,8S,10R)-7-Benzyloxymethyl-8-methoxy-2,2,10-trimethyl-1,3,6-trioxa-spiro[4.5]decane-4-carbonyl)-piperidine-2-carboxylic acid methyl ester (123492-32-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) NaH / 1.) THF, 0 deg C 2.) 36 h

2: 1.) NaH / THF, room temp., 8h

3: AcOH, H₂SO₄ / H₂O / 1.5 h / 90 °C

4: Ac₂O, DMSO / 24 h / Ambient temperature

5: 1.) LDA / THF, -78 deg C, 3h

6: PPTs, H₂O / tetrahydrofuran / 5 h / 55 °C

7: P₂O₅ / 15 h / Ambient temperature

8: LiOH / methanol; H₂O / 6 h / Ambient temperature

9: SOCl₂ / pyridine / 0.17 h / Ambient temperature

10: Et₃N / 2 h / Ambient temperature

With lithium hydroxide; thionyl chloride; sulfuric acid; water; phosphorus pentoxide; pyridinium p-toluenesulfonate; acetic anhydride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; water;

DOI:10.1016/S0040-4039(00)95278-X

upstream raw materials:

(S)-methyl pipecolinate hydrochloride

Methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside

(2R,3S,5R,6S)-2-Hydroxymethyl-6-methoxy-5-methyl-tetrahydro-pyran-3-ol

benzyl bromide

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