2,4,6-trideoxy-3,5-O-(S)-(p-methoxybenzylidene)-2,4,6-tri-C-methyl-7-S-phenyl-7-thio-L-glycero-L-ido-heptose trimethylene dithioacetal

Base Information

• Chemical Name: 2,4,6-trideoxy-3,5-O-(S)-(p-methoxybenzylidene)-2,4,6-tri-C-methyl-7-S-phenyl-7-thio-L-glycero-L-ido-heptose trimethylene dithioacetal
• CAS No.: 129908-77-6
• Molecular Formula: C₂₇H₃₆O₃S₃
• Molecular Weight: 504.779
• Mol file: 129908-77-6.mol

Synonyms:2,4,6-trideoxy-3,5-O-(S)-(p-methoxybenzylidene)-2,4,6-tri-C-methyl-7-S-phenyl-7-thio-L-glycero-L-ido-heptose trimethylene dithioacetal

Chemical Property of 2,4,6-trideoxy-3,5-O-(S)-(p-methoxybenzylidene)-2,4,6-tri-C-methyl-7-S-phenyl-7-thio-L-glycero-L-ido-heptose trimethylene dithioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4,6-trideoxy-3,5-O-(S)-(p-methoxybenzylidene)-2,4,6-tri-C-methyl-7-S-phenyl-7-thio-L-glycero-L-ido-heptose trimethylene dithioacetal

There total 8 articles about 2,4,6-trideoxy-3,5-O-(S)-(p-methoxybenzylidene)-2,4,6-tri-C-methyl-7-S-phenyl-7-thio-L-glycero-L-ido-heptose trimethylene dithioacetal 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: 86.0%

2,4,6-trideoxy-3-O-(p-methoxybenzyl)-2,4,6-tri-C-methyl-7-S-phenyl-7-thio-L-glycero-L-ido-heptose trimethylene dithioacetal (129908-76-5) → 2,4,6-trideoxy-3,5-O-(S)-(p-methoxybenzylidene)-2,4,6-tri-C-methyl-7-S-phenyl-7-thio-L-glycero-L-ido-heptose trimethylene dithioacetal (129908-77-6)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 0.166667h; molecular sieves 3 Angstroem;

DOI:10.1016/0008-6215(90)84192-W

Reference yield:

2,4-dideoxy-5,6-O-isopropylidene-2,4-di-C-methyl-D-glucose trimethylene dithioacetal (100699-20-5) → 2,4,6-trideoxy-3,5-O-(S)-(p-methoxybenzylidene)-2,4,6-tri-C-methyl-7-S-phenyl-7-thio-L-glycero-L-ido-heptose trimethylene dithioacetal (129908-77-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) sodium hydride / 1) N,N-dimethylformamide, 4h, 20 deg C, 2) 15h

2: 87 percent / aq. hydrochloric acid / tetrahydrofuran / 80 h / 20 °C

3: 86 percent / potassium acetate, lead tetra-acetate / acetonitrile / 0.05 h / -25 °C

5: 96 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 20 °C

6: 94 percent / tributyl phosphine / pyridine / 3 h / 20 °C

7: 86 percent / DDQ / CH₂Cl₂ / 0.17 h / molecular sieves 3 Angstroem

With lead(IV) acetate; hydrogenchloride; lithium aluminium tetrahydride; tributylphosphine; potassium acetate; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile;

DOI:10.1016/0008-6215(90)84192-W

Reference yield:

2,4-dideoxy-3-O-(p-methoxybenzyl)-2,4-di-C-methyl-l-xylo-pentodialdose 5-(trimethylene dithioacetal) (129908-73-2) → 2,4,6-trideoxy-3,5-O-(S)-(p-methoxybenzylidene)-2,4,6-tri-C-methyl-7-S-phenyl-7-thio-L-glycero-L-ido-heptose trimethylene dithioacetal (129908-77-6)

Guidance literature:

Multi-step reaction with 4 steps

2: 96 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 20 °C

3: 94 percent / tributyl phosphine / pyridine / 3 h / 20 °C

4: 86 percent / DDQ / CH₂Cl₂ / 0.17 h / molecular sieves 3 Angstroem

With lithium aluminium tetrahydride; tributylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1016/0008-6215(90)84192-W

upstream raw materials:

2,4,6-trideoxy-3-O-(p-methoxybenzyl)-2,4,6-tri-C-methyl-7-S-phenyl-7-thio-L-glycero-L-ido-heptose trimethylene dithioacetal

2,4-dideoxy-5,6-O-isopropylidene-2,4-di-C-methyl-D-glucose trimethylene dithioacetal

2,4-dideoxy-3-O-(p-methoxybenzyl)-2,4-di-C-methyl-l-xylo-pentodialdose 5-(trimethylene dithioacetal)

2,4-dideoxy-3-O-(p-methoxybenzyl)-2,4-di-C-methyl-D-glucose trimethylene dithioacetal

Downstream raw materials:

1,2,3,5,7-pentadeoxy-4,6-O-(R)-(p-methoxybenzylidene)-3,5,7-tri-C-methyl-8-S-phenyl-8-thio-L-glycero-L-ido-oct-1-enitol

1,2,3,5,7,8-hexadeoxy-4,6-O-(R)-(p-methoxybenzylidene)-3,5,7-tri-C-methyl-8-C-phenylsulfonyl-L-glycero-L-ido-oct-1-enitol