methyl (3S,4E,6R)-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,6R)-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.:608530-03-6
Molecular Formula:C₃₂H₄₀O₁₀
Molecular Weight:584.664
Hs Code.:

Synonyms:methyl (3S,4E,6R)-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,6R)-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,6R)-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 7 articles about methyl (3S,4E,6R)-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: 80.0%

: 108-59-8
malonic acid dimethyl ester

: 608530-02-5
(1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-4-O-(ethoxycarbonyl)pent-2-ene-1,4-diol

: 608530-03-6
methyl (3S,4E,6R)-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:: malonic acid dimethyl ester; With sodium hydride; In tetrahydrofuran;

(1R,4R)-1-[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]-4-O-(ethoxycarbonyl)pent-2-ene-1,4-diol; palladium diacetate; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; at 20 ℃; Further stages.;
DOI:10.1002/ejoc.200300255

Reference yield:

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

: 608530-03-6
methyl (3S,4E,6R)-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: 343 mg / MgBr₂; methyllithium / diethyl ether / -30 - 20 °C

2.1: 90 percent / DEAD; triphenylphosphane / tetrahydrofuran / 1 h / 0 °C

3.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

4.1: 90 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

5.1: 70 percent / K₂CO₃ / methanol / 0.25 h / 20 °C

6.1: 70 percent / hydrogen; pyridine / Pd/C / ethyl acetate / 20 °C

7.1: NaH / tetrahydrofuran

7.2: 80 percent / Pd(OAc)2; bis(diphenylphosphanyl)ethane / tetrahydrofuran / 20 °C

With pyridine; tetrabutyl ammonium fluoride; methyllithium; hydrogen; sodium hydride; potassium carbonate; triphenylphosphine; magnesium bromide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1002/ejoc.200300255

Reference yield:

: 256397-92-9
(1S,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

: 608530-03-6
methyl (3S,4E,6R)-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 6 steps

1.1: 90 percent / DEAD; triphenylphosphane / tetrahydrofuran / 1 h / 0 °C

2.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

3.1: 90 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

4.1: 70 percent / K₂CO₃ / methanol / 0.25 h / 20 °C

5.1: 70 percent / hydrogen; pyridine / Pd/C / ethyl acetate / 20 °C

6.1: NaH / tetrahydrofuran

6.2: 80 percent / Pd(OAc)2; bis(diphenylphosphanyl)ethane / tetrahydrofuran / 20 °C

With pyridine; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1002/ejoc.200300255