7,10-anhydro-2,3,5-tri-O-benzyl-11-bromo-4,6,8,10,11-pentadeoxy-4-C-(1'-formyl)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-D-(or L-)glycero-L-talo-L-altro-1',1-pyranose-undecitol

Base Information

• Chemical Name: 7,10-anhydro-2,3,5-tri-O-benzyl-11-bromo-4,6,8,10,11-pentadeoxy-4-C-(1'-formyl)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-D-(or L-)glycero-L-talo-L-altro-1',1-pyranose-undecitol
• CAS No.: 128062-06-6
• Molecular Formula: C₄₆H₅₇BrO₉
• Molecular Weight: 833.857
• Mol file: 128062-06-6.mol

Synonyms:7,10-anhydro-2,3,5-tri-O-benzyl-11-bromo-4,6,8,10,11-pentadeoxy-4-C-(1'-formyl)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-D-(or L-)glycero-L-talo-L-altro-1',1-pyranose-undecitol

Chemical Property of 7,10-anhydro-2,3,5-tri-O-benzyl-11-bromo-4,6,8,10,11-pentadeoxy-4-C-(1'-formyl)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-D-(or L-)glycero-L-talo-L-altro-1',1-pyranose-undecitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7,10-anhydro-2,3,5-tri-O-benzyl-11-bromo-4,6,8,10,11-pentadeoxy-4-C-(1'-formyl)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-D-(or L-)glycero-L-talo-L-altro-1',1-pyranose-undecitol

There total 18 articles about 7,10-anhydro-2,3,5-tri-O-benzyl-11-bromo-4,6,8,10,11-pentadeoxy-4-C-(1'-formyl)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-D-(or L-)glycero-L-talo-L-altro-1',1-pyranose-undecitol 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: 94.0%

2,3,5,9-tetra-O-benzyl-4,6,8-10,11-pentadeoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-L-galacto-L-altro-1,1':1',7-bipyranoside-undecitol (115072-44-1) → 7,10-anhydro-2,3,5-tri-O-benzyl-11-bromo-4,6,8,10,11-pentadeoxy-4-C-(1'-formyl)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-D-(or L-)glycero-L-talo-L-altro-1',1-pyranose-undecitol (128062-06-6)

Guidance literature:

With N-Bromosuccinimide; sodium hydrogencarbonate; In acetonitrile; at 0 ℃; for 0.166667h;

Reference yield:

((2S,3R,4S,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-methanol (128041-98-5) → 7,10-anhydro-2,3,5-tri-O-benzyl-11-bromo-4,6,8,10,11-pentadeoxy-4-C-(1'-formyl)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-D-(or L-)glycero-L-talo-L-altro-1',1-pyranose-undecitol (128062-06-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) DMSO, oxalylchloride, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 20 min, 2) -78 deg C -> deg C

2: 2) DMSO, oxalylchloride, 3) Et₃N

3: 82 percent / tetrahydrofuran / Ambient temperature

4: 70 percent / 9-borabicyclo<3.3.1>nonane / tetrahydrofuran / 1 h / Ambient temperature

5: 87 percent / pyridinium chlorochromate, Celite, NaOAc, Florisil / CH₂Cl₂ / 1 h / Ambient temperature

6: 2) NaH, tetrabutylammonium iodide / 1) THF, -90 -> 0 deg C, 2) DMF, 0 deg C, 20 min, 3) 0 deg C -> r.t., 1h

7: 94 percent / NBS, NaHCO₃ / acetonitrile / 0.17 h / 0 °C

With florisil; N-Bromosuccinimide; 9-borabicyclo[3.3.1]nonane dimer; Chloro-oxo-acetic acid; Celite; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; acetonitrile;

Reference yield:

2,3,5-tri-O-benzyl-4,6,9-trideoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2-C-methyl-8-ulo-D-talo-L-threo-1,1':1',7-bipyranoside-nonitol (128042-00-2) → 7,10-anhydro-2,3,5-tri-O-benzyl-11-bromo-4,6,8,10,11-pentadeoxy-4-C-(1'-formyl)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-D-(or L-)glycero-L-talo-L-altro-1',1-pyranose-undecitol (128062-06-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / tetrahydrofuran / Ambient temperature

2: 70 percent / 9-borabicyclo<3.3.1>nonane / tetrahydrofuran / 1 h / Ambient temperature

3: 87 percent / pyridinium chlorochromate, Celite, NaOAc, Florisil / CH₂Cl₂ / 1 h / Ambient temperature

4: 2) NaH, tetrabutylammonium iodide / 1) THF, -90 -> 0 deg C, 2) DMF, 0 deg C, 20 min, 3) 0 deg C -> r.t., 1h

5: 94 percent / NBS, NaHCO₃ / acetonitrile / 0.17 h / 0 °C

With florisil; N-Bromosuccinimide; 9-borabicyclo[3.3.1]nonane dimer; Celite; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; acetonitrile;

upstream raw materials:

2,3,5,9-tetra-O-benzyl-4,6,8-10,11-pentadeoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-L-galacto-L-altro-1,1':1',7-bipyranoside-undecitol

((2S,3R,4S,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-3-methoxymethoxymethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-2-yl)-methanol

2,3,5-tri-O-benzyl-4,6-dideoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2-C-methyl-8-aldehydo-D-talo-L-threo-1,1':1',7-bipyranoside-ocitol

2,3,5-tri-O-benzyl-4,6,9-trideoxy-4-C-(1'-formyl)-(1'S)-6-C-(1-methoxymethoxymethyl)-2-C-methyl-8-ulo-D-talo-L-threo-1,1':1',7-bipyranoside-nonitol

Downstream raw materials:

7,10-anhydro-2,3,5-tri-O-benzyl-11-bromo-4,6,8,11-tetradeoxy-4-C-(1'-formyl)-6-C-(1-methoxymethoxymethyl)-2,8,10-tri-C-methyl-D-(or L-)glycero-L-talo-L-altro-1',1-pyranose-undecitol