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

Base Information

• Chemical Name: Benzoic acid (S)-methoxycarbonyl-((2R,4R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester
• CAS No.: 104432-02-2
• Molecular Formula: C₂₅H₃₀O₆Se
• Molecular Weight: 505.47
• Mol file: 104432-02-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 18 articles about Benzoic acid (S)-methoxycarbonyl-((2R,4R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-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: 94.0%

phenyl selenocyanate (2179-79-5) + Benzoic acid (S)-((2R,4R,5R,6R)-4-hydroxymethyl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-methoxycarbonyl-methyl ester (104432-01-1) → Benzoic acid (S)-methoxycarbonyl-((2R,4R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester (104432-02-2)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; at 0 ℃;

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)-methoxycarbonyl-((2R,4R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester (104432-02-2)

Guidance literature:

Multi-step reaction with 12 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

10: HgO, HgCl₂ / H₂O; acetonitrile

11: Zn(BH₄)2 / diethyl ether / 91percent from INO 1240

12: 94 percent / Bu₃P / tetrahydrofuran / 0 °C

With hydrogenchloride; dmap; titanium(III) chloride; zinc(II) tetrahydroborate; tributylphosphine; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; N-benzyl-trimethylammonium hydroxide; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; mercury dichloride; mercury(II) oxide; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; acetonitrile; 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)-methoxycarbonyl-((2R,4R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester (104432-02-2)

Guidance literature:

Multi-step reaction with 13 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

11: HgO, HgCl₂ / H₂O; acetonitrile

12: Zn(BH₄)2 / diethyl ether / 91percent from INO 1240

13: 94 percent / Bu₃P / tetrahydrofuran / 0 °C

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

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

upstream raw materials:

phenyl selenocyanate

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

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)-carboxy-((2R,4R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester

(S)-2-methoxy-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-oxoethyl benzoate

mycalamide A