(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

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-yne-1,4-diol
CAS No.:256398-00-2
Molecular Formula:C₃₀H₃₆O₉
Molecular Weight:540.61
Hs Code.:

Synonyms:(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

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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-yne-1,4-diol

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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-yne-1,4-diol

There total 6 articles about (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 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: 91.0%

: 256397-99-6
(1S,4R)-1-O-allyloxycarbonyl-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-yne-1,4-diol

Guidance literature:: With palladium diacetate; trisodium tris(3-sulfophenyl)phosphine; diethylamine; In water; acetonitrile; at 20 ℃;
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

: 256398-00-2
(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

Guidance literature:: Multi-step reaction with 6 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

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

: 256398-00-2
(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

Guidance literature:: Multi-step reaction with 5 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

With pyridine; palladium diacetate; tetrabutyl ammonium fluoride; trisodium tris(3-sulfophenyl)phosphine; methyllithium; diethylamine; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; 1.1: Metallation / 1.2: Addition / 2.1: Acylation / 3.1: deprotection / 4.1: Acylation / 5.1: Hydrolysis;
DOI:10.1002/(SICI)1099-0690(199911)1999:11<2885::AID-EJOC2885>3.0.CO;2-J