(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

Base Information

• Chemical Name: (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
• CAS No.: 256398-01-3
• Molecular Formula: C₃₀H₃₈O₉
• Molecular Weight: 542.626

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 7 articles about (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 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: 56.0%

(1S,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-4-O-ethoxycarbonylpent-2-yne-1,4-diol (256398-00-2) → (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 (256398-01-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In pyridine; methanol; at 20 ℃; for 1h;

DOI:10.1002/(SICI)1099-0690(199911)1999:11<2885::AID-EJOC2885>3.0.CO;2-J

Reference yield:

[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]methanol (75858-32-1) → (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 (256398-01-3)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; palladium diacetate; oxalyl dichloride; tetrabutyl ammonium fluoride; trisodium tris(3-sulfophenyl)phosphine; methyllithium; hydrogen; dimethyl sulfoxide; diethylamine; triethylamine; 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;

DOI:10.1002/(SICI)1099-0690(199911)1999:11<2885::AID-EJOC2885>3.0.CO;2-J

Reference yield:

[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]aldehyde (256397-91-8) → (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 (256398-01-3)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; palladium diacetate; tetrabutyl ammonium fluoride; trisodium tris(3-sulfophenyl)phosphine; methyllithium; hydrogen; diethylamine; 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;

DOI:10.1002/(SICI)1099-0690(199911)1999:11<2885::AID-EJOC2885>3.0.CO;2-J

upstream raw materials:

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

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

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

(1S,4R)-1-O-allyloxycarbonyl-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]pent-2-yne-1,4-diol

Downstream raw materials:

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

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

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