(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

Base Information

Chemical Name:(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
CAS No.:256397-98-5
Molecular Formula:C₃₁H₃₆O₉
Molecular Weight:552.621
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 4 articles about (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 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: 93.0%

: 256397-96-3
(1S,4R)-1-O-allyloxycarbonyl-4-O-tert-butyldimethylsilyl-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]pent-2-yne-1,4-diol

: 256397-98-5
(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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 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

: 256397-98-5
(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

Guidance literature:: Multi-step reaction with 4 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

With pyridine; oxalyl dichloride; tetrabutyl ammonium fluoride; methyllithium; dimethyl sulfoxide; triethylamine; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Oxidation / 2.1: Metallation / 2.2: Addition / 3.1: Acylation / 4.1: deprotection;
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

: 256397-98-5
(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

Guidance literature:: Multi-step reaction with 3 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

With pyridine; tetrabutyl ammonium fluoride; methyllithium; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Metallation / 1.2: Addition / 2.1: Acylation / 3.1: deprotection;
DOI:10.1002/(SICI)1099-0690(199911)1999:11<2885::AID-EJOC2885>3.0.CO;2-J