(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

Base Information

Chemical Name:(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
CAS No.:256397-96-3
Molecular Formula:C₃₇H₅₀O₉Si
Molecular Weight:666.884
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 3 articles about (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 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: 99.0%

: 2937-50-0
Allyl chloroformate

: 256397-94-1
(1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-4-O-(tert-butyldimethylsilyl)pent-2-yne-1,4-diol

: 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

Guidance literature:: With pyridine; In dichloromethane; 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

: 256397-96-3
(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

Guidance literature:: Multi-step reaction with 3 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

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

: 256397-96-3
(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

Guidance literature:: Multi-step reaction with 2 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

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