Benzoic acid (S)-((2R,4R,5R,6R)-4-[1,3]dithiolan-2-yl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-methoxycarbonyl-methyl ester

Base Information

• Chemical Name: Benzoic acid (S)-((2R,4R,5R,6R)-4-[1,3]dithiolan-2-yl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-methoxycarbonyl-methyl ester
• CAS No.: 104432-00-0
• Molecular Formula: C₂₁H₂₈O₆S₂
• Molecular Weight: 440.582

Synonyms:Benzoic acid (S)-((2R,4R,5R,6R)-4-[1,3]dithiolan-2-yl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-methoxycarbonyl-methyl ester

Chemical Property of Benzoic acid (S)-((2R,4R,5R,6R)-4-[1,3]dithiolan-2-yl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-methoxycarbonyl-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Benzoic acid (S)-((2R,4R,5R,6R)-4-[1,3]dithiolan-2-yl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-methoxycarbonyl-methyl ester

There total 15 articles about Benzoic acid (S)-((2R,4R,5R,6R)-4-[1,3]dithiolan-2-yl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-methoxycarbonyl-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: 86.0%

(S)-((2R,4R,5R,6R)-4-[1,3]Dithiolan-2-yl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-hydroxy-acetic acid methyl ester (104431-99-4) + benzoyl chloride (98-88-4) → Benzoic acid (S)-((2R,4R,5R,6R)-4-[1,3]dithiolan-2-yl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-methoxycarbonyl-methyl ester (104432-00-0)

Guidance literature:

With dmap; In pyridine;

DOI:10.1016/S0040-4039(00)99028-2

Reference yield:

syn-(5R,6R)-5,6-Dimethyl-5,6-dihydropyran-2-one (104486-83-1) → Benzoic acid (S)-((2R,4R,5R,6R)-4-[1,3]dithiolan-2-yl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-methoxycarbonyl-methyl ester (104432-00-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 92 percent / Triton B

2: TiCl₃, Et₃N

3: c. HCl / CH₂Cl₂ / 70percent yield from INO 1110

4: 81 percent / BF₃:Et₂O / CH₂Cl₂ / Ambient temperature

5: LDA / tetrahydrofuran / 1.) -78 deg C, 2.) -20 deg C

6: CSA / CH₂Cl₂; methanol

7: DMSO, DCC / pyridine; trifluoroacetic acid; diethyl ether / 91percent yield from INO 1150

8: Zn(BH₄)2 / diethyl ether / -78 °C

9: 86 percent / DMAP / pyridine

With hydrogenchloride; dmap; titanium(III) chloride; zinc(II) tetrahydroborate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; N-benzyl-trimethylammonium hydroxide; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; trifluoroacetic acid;

DOI:10.1016/S0040-4039(00)99028-2

Reference yield:

(4S,5R)-3,5-Dihydroxy-4-methyl-hexanoic acid tert-butyl ester (334685-79-9) → Benzoic acid (S)-((2R,4R,5R,6R)-4-[1,3]dithiolan-2-yl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-methoxycarbonyl-methyl ester (104432-00-0)

Guidance literature:

Multi-step reaction with 10 steps

1: p-TsOH / benzene / Heating; 81percent yield from INO 1060

2: 92 percent / Triton B

3: TiCl₃, Et₃N

4: c. HCl / CH₂Cl₂ / 70percent yield from INO 1110

5: 81 percent / BF₃:Et₂O / CH₂Cl₂ / Ambient temperature

6: LDA / tetrahydrofuran / 1.) -78 deg C, 2.) -20 deg C

7: CSA / CH₂Cl₂; methanol

8: DMSO, DCC / pyridine; trifluoroacetic acid; diethyl ether / 91percent yield from INO 1150

9: Zn(BH₄)2 / diethyl ether / -78 °C

10: 86 percent / DMAP / pyridine

With hydrogenchloride; dmap; titanium(III) chloride; zinc(II) tetrahydroborate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; N-benzyl-trimethylammonium hydroxide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; trifluoroacetic acid; benzene;

DOI:10.1016/S0040-4039(00)99028-2

upstream raw materials:

(S)-((2R,4R,5R,6R)-4-[1,3]Dithiolan-2-yl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-hydroxy-acetic acid methyl ester

benzoyl chloride

syn-(5R,6R)-5,6-Dimethyl-5,6-dihydropyran-2-one

(4S,5R)-3,5-Dihydroxy-4-methyl-hexanoic acid tert-butyl ester

Downstream raw materials:

(S)-Hydroxy-((2R,4R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester

Benzoic acid (S)-((2R,4R,5R,6R)-4-hydroxymethyl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-methoxycarbonyl-methyl ester

Benzoic acid (S)-methoxycarbonyl-((2R,4R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester

Benzoic acid (S)-chlorocarbonyl-((2R,4R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester

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