methyl (3S,4E,6R)-6-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-6-hydroxy-2-(methoxycarbonyl)-3-methylhex-4-enoate

Base Information

Chemical Name:methyl (3S,4E,6R)-6-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-6-hydroxy-2-(methoxycarbonyl)-3-methylhex-4-enoate
CAS No.:608529-98-2
Molecular Formula:C₄₄H₅₀O₁₀
Molecular Weight:738.875
Hs Code.:

Synonyms:methyl (3S,4E,6R)-6-(2,3,4,6-tetra-O-benzyl-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-(2,3,4,6-tetra-O-benzyl-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-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-6-hydroxy-2-(methoxycarbonyl)-3-methylhex-4-enoate

There total 6 articles about methyl (3S,4E,6R)-6-(2,3,4,6-tetra-O-benzyl-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: 43.0%

: 108-59-8
malonic acid dimethyl ester

: 608530-13-8
(1R,2Z,4R)-1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-4-O-(ethoxycarbonyl)pent-2-ene-1,4-diol

: 608529-98-2
methyl (3S,4E,6R)-6-(2,3,4,6-tetra-O-benzyl-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,2Z,4R)-1-(2,3,4,6-tetra-O-benzyl-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 ℃; for 1h; Further stages.;
DOI:10.1002/ejoc.200300255

Reference yield:

: 608529-97-1
(1R,4R)-1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-4-O-(ethoxycarbonyl)pent-2-yne-1,4-diol

: 608529-98-2
methyl (3S,4E,6R)-6-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-6-hydroxy-2-(methoxycarbonyl)-3-methylhex-4-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 70 percent / hydrogen; pyridine / Pd/C / methanol / 20 °C

2.1: NaH / tetrahydrofuran

2.2: 43 percent / Pd(OAc)2; bis(diphenylphosphanyl)ethane / tetrahydrofuran / 1 h / 20 °C

With pyridine; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol;
DOI:10.1002/ejoc.200300255

Reference yield:

: 608530-11-6
(1R,4R)-1-O-allyloxycarbonyl-1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)pent-2-yne-1,4-diol

: 608529-98-2
methyl (3S,4E,6R)-6-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-6-hydroxy-2-(methoxycarbonyl)-3-methylhex-4-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 92 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

2.1: 83 percent / Pd(OAc)2; TPPTS; diethylamine / H₂O; acetonitrile / 20 °C

3.1: 70 percent / hydrogen; pyridine / Pd/C / methanol / 20 °C

4.1: NaH / tetrahydrofuran

4.2: 43 percent / Pd(OAc)2; bis(diphenylphosphanyl)ethane / tetrahydrofuran / 1 h / 20 °C

With pyridine; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine; hydrogen; sodium hydride; diethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
DOI:10.1002/ejoc.200300255