(R)-4-[(R)-3-Hydroxy-4-((2R,3R,7R,10S)-2,3,10-trimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-butyryl]-3-(4-methoxy-benzyl)-thiazolidin-2-one

Base Information

• Chemical Name: (R)-4-[(R)-3-Hydroxy-4-((2R,3R,7R,10S)-2,3,10-trimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-butyryl]-3-(4-methoxy-benzyl)-thiazolidin-2-one
• CAS No.: 101860-56-4
• Molecular Formula: C₂₅H₃₅NO₇S
• Molecular Weight: 493.621
• Mol file: 101860-56-4.mol

Synonyms:

Chemical Property of (R)-4-[(R)-3-Hydroxy-4-((2R,3R,7R,10S)-2,3,10-trimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-butyryl]-3-(4-methoxy-benzyl)-thiazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-[(R)-3-Hydroxy-4-((2R,3R,7R,10S)-2,3,10-trimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-butyryl]-3-(4-methoxy-benzyl)-thiazolidin-2-one

There total 21 articles about (R)-4-[(R)-3-Hydroxy-4-((2R,3R,7R,10S)-2,3,10-trimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-butyryl]-3-(4-methoxy-benzyl)-thiazolidin-2-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: 58.0%

((2R,3R,7R,10S)-2,3,10-Trimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-acetaldehyde (101860-55-3) + (-)-4-acetyl-3-(4-methoxybenzyl)-thiazolidinon-2-one (101860-51-9) → (R)-4-[3-Hydroxy-4-((2R,3R,7R,10S)-2,3,10-trimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-butyryl]-3-(4-methoxy-benzyl)-thiazolidin-2-one (101860-56-4,101977-01-9)

Guidance literature:

With LiN(SiMe)3; zinc(II) chloride; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/ja00269a056

Reference yield:

tetrahydro-6-(2-propenyl)pyran-2(2H)-one (87086-60-0,34686-69-6) → (R)-4-[3-Hydroxy-4-((2R,3R,7R,10S)-2,3,10-trimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-butyryl]-3-(4-methoxy-benzyl)-thiazolidin-2-one (101860-56-4,101977-01-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA / tetrahydrofuran / 1.) -78 deg C; 2.) -78 deg C to r.t.

2: 42 percent / CSA / benzene / Heating

3: O₃

4: 58 percent / 1.) LiN(SiMe)3; 2.) ZnCl₂ / tetrahydrofuran / -78 °C

With LiN(SiMe)3; camphor-10-sulfonic acid; ozone; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; benzene;

DOI:10.1021/ja00269a056

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (R)-4-[3-Hydroxy-4-((2R,3R,7R,10S)-2,3,10-trimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-butyryl]-3-(4-methoxy-benzyl)-thiazolidin-2-one (101860-56-4,101977-01-9)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH / dimethylformamide / 0 deg C to r.t.

2: 1N KOH

3: MeLi / -78 deg C to r.t.

4: 58 percent / 1.) LiN(SiMe)3; 2.) ZnCl₂ / tetrahydrofuran / -78 °C

With potassium hydroxide; LiN(SiMe)3; methyllithium; sodium hydride; zinc(II) chloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja00269a056

upstream raw materials:

((2R,3R,7R,10S)-2,3,10-Trimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-acetaldehyde

(-)-4-acetyl-3-(4-methoxybenzyl)-thiazolidinon-2-one

tetrahydro-6-(2-propenyl)pyran-2(2H)-one

p-Methoxybenzyl bromide

Downstream raw materials:

(S)-4-{(2R,4R,6R)-4,6-Dihydroxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-2-methyl-butyric acid (1R,2R)-2-hydroxy-1-methyl-propyl ester

(S)-4-{(2R,4S,6R)-4,6-Dihydroxy-6-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-tetrahydro-pyran-2-yl}-2-methyl-butyric acid (1R,2R)-2-hydroxy-1-methyl-propyl ester

latrunculin A

latrunculin B