(3S,4S,5R,6R)-5-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-di(benzyloxy)-7-heptanolide

Base Information

Chemical Name:(3S,4S,5R,6R)-5-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-di(benzyloxy)-7-heptanolide
CAS No.:164729-49-1
Molecular Formula:C₅₄H₅₆O₁₁
Molecular Weight:881.032
Hs Code.:

Synonyms:(3S,4S,5R,6R)-5-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-di(benzyloxy)-7-heptanolide

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Chemical Property of (3S,4S,5R,6R)-5-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-di(benzyloxy)-7-heptanolide

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Technology Process of (3S,4S,5R,6R)-5-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-di(benzyloxy)-7-heptanolide

There total 10 articles about (3S,4S,5R,6R)-5-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-di(benzyloxy)-7-heptanolide 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: 71.0%

: (2S,3R,4S,5S)-2,4-dibenzyloxy-5-hydroxy-3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyloxy)cyclohexanone

: 164729-49-1
(3S,4S,5R,6R)-5-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-di(benzyloxy)-7-heptanolide

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 16h; Ambient temperature;
DOI:10.1016/0040-4020(94)01047-4

Reference yield:

: 100-39-0
benzyl bromide

: 164729-49-1
(3S,4S,5R,6R)-5-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-di(benzyloxy)-7-heptanolide

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaH / 1.) DMF, r.t., 10 min; 2.) DMF, r.t., 30 min

2: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / Ambient temperature

3: 97 percent / DMAP, pyridine / 12 h / Ambient temperature

4: 1.) Bu₄NI, NaI, molecular sieves 4A; 2.) DBU / 1.) DMSO, 80 deg C, 2 h; 2.) DMSO, 80 deg C, 2 h

5: 61 percent / mercury(II) trifluoroacetate / acetone; H₂O / 12 h / Ambient temperature

6: 71 percent / m-CPBA / CH₂Cl₂ / 16 h / Ambient temperature

With pyridine; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; mercury(II) trifluoroacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; dichloromethane; water; acetone;
DOI:10.1016/0040-4020(94)01047-4

Reference yield:

: 126330-73-2
2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside

: 164729-49-1
(3S,4S,5R,6R)-5-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-di(benzyloxy)-7-heptanolide

Guidance literature:: Multi-step reaction with 9 steps

1: 51 percent / MeI, molecular sieves 4A / CH₂Cl₂ / 120 h / 50 °C

2: 95 percent / p-TSA / acetone; H₂O / 8 h / Ambient temperature

3: 96 percent / DMAP, pyridine / 2 h / Ambient temperature

4: 1.) NaH / 1.) DMF, r.t., 10 min; 2.) DMF, r.t., 30 min

5: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / Ambient temperature

6: 97 percent / DMAP, pyridine / 12 h / Ambient temperature

7: 1.) Bu₄NI, NaI, molecular sieves 4A; 2.) DBU / 1.) DMSO, 80 deg C, 2 h; 2.) DMSO, 80 deg C, 2 h

8: 61 percent / mercury(II) trifluoroacetate / acetone; H₂O / 12 h / Ambient temperature

9: 71 percent / m-CPBA / CH₂Cl₂ / 16 h / Ambient temperature

With pyridine; dmap; 4 A molecular sieve; tetrabutyl ammonium fluoride; mercury(II) trifluoroacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; sodium iodide; methyl iodide; In tetrahydrofuran; dichloromethane; water; acetone;
DOI:10.1016/0040-4020(94)01047-4