methyl (3S,4E,6S)-6-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-6-hydroxy-2-methoxycarbonyl-3-methylhex-4-enoate

Base Information

Chemical Name:methyl (3S,4E,6S)-6-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-6-hydroxy-2-methoxycarbonyl-3-methylhex-4-enoate
CAS No.:256398-02-4
Molecular Formula:C₃₂H₄₀O₁₀
Molecular Weight:584.664
Hs Code.:

Synonyms:methyl (3S,4E,6S)-6-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-6-hydroxy-2-methoxycarbonyl-3-methylhex-4-enoate

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Chemical Property of methyl (3S,4E,6S)-6-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-6-hydroxy-2-methoxycarbonyl-3-methylhex-4-enoate

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Technology Process of methyl (3S,4E,6S)-6-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-6-hydroxy-2-methoxycarbonyl-3-methylhex-4-enoate

There total 8 articles about methyl (3S,4E,6S)-6-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-6-hydroxy-2-methoxycarbonyl-3-methylhex-4-enoate 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: 60.0%

: 108-59-8
malonic acid dimethyl ester

: 256398-01-3
(1S,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-4-O-ethoxycarbonylpent-2-ene-1,4-diol

: 256398-02-4
methyl (3S,4E,6S)-6-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-6-hydroxy-2-methoxycarbonyl-3-methylhex-4-enoate

Guidance literature:: With palladium diacetate; sodium hydride; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1002/(SICI)1099-0690(199911)1999:11<2885::AID-EJOC2885>3.0.CO;2-J

Reference yield:

: 75858-32-1
[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]methanol

: 256398-02-4
methyl (3S,4E,6S)-6-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-6-hydroxy-2-methoxycarbonyl-3-methylhex-4-enoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 74 percent / oxalyl chloride; DMSO; NEt₃ / CH₂Cl₂ / 8 h / -45 °C

2.1: MeLi; MgBr₂ / diethyl ether / 0.5 h / -5 °C

2.2: MgBr₂ / diethyl ether / -60 - 20 °C

3.1: 99 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

4.1: 93 percent / Bu₄NF / tetrahydrofuran / 0 - 20 °C

5.1: 94 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

6.1: 91 percent / Pd(OAc)2; TPPTS; Et₂NH / acetonitrile; H₂O / 20 °C

7.1: 56 percent / H₂ / Pd/C / methanol; pyridine / 1 h / 20 °C

8.1: 60 percent / Pd(OAc)2; dppe; NaH / tetrahydrofuran / 1 h / 20 °C

With pyridine; palladium diacetate; oxalyl dichloride; tetrabutyl ammonium fluoride; trisodium tris(3-sulfophenyl)phosphine; methyllithium; hydrogen; sodium hydride; dimethyl sulfoxide; diethylamine; triethylamine; 1,2-bis-(diphenylphosphino)ethane; magnesium bromide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; acetonitrile; 1.1: Oxidation / 2.1: Metallation / 2.2: Addition / 3.1: Acylation / 4.1: deprotection / 5.1: Acylation / 6.1: Hydrolysis / 7.1: Hydrogenation / 8.1: Alkylation;
DOI:10.1002/(SICI)1099-0690(199911)1999:11<2885::AID-EJOC2885>3.0.CO;2-J

Reference yield:

: 256397-91-8
[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]aldehyde

: 256398-02-4
methyl (3S,4E,6S)-6-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-6-hydroxy-2-methoxycarbonyl-3-methylhex-4-enoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: MeLi; MgBr₂ / diethyl ether / 0.5 h / -5 °C

1.2: MgBr₂ / diethyl ether / -60 - 20 °C

2.1: 99 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

3.1: 93 percent / Bu₄NF / tetrahydrofuran / 0 - 20 °C

4.1: 94 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

5.1: 91 percent / Pd(OAc)2; TPPTS; Et₂NH / acetonitrile; H₂O / 20 °C

6.1: 56 percent / H₂ / Pd/C / methanol; pyridine / 1 h / 20 °C

7.1: 60 percent / Pd(OAc)2; dppe; NaH / tetrahydrofuran / 1 h / 20 °C

With pyridine; palladium diacetate; tetrabutyl ammonium fluoride; trisodium tris(3-sulfophenyl)phosphine; methyllithium; hydrogen; sodium hydride; diethylamine; 1,2-bis-(diphenylphosphino)ethane; magnesium bromide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; acetonitrile; 1.1: Metallation / 1.2: Addition / 2.1: Acylation / 3.1: deprotection / 4.1: Acylation / 5.1: Hydrolysis / 6.1: Hydrogenation / 7.1: Alkylation;
DOI:10.1002/(SICI)1099-0690(199911)1999:11<2885::AID-EJOC2885>3.0.CO;2-J