2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside
• CAS No.: 153718-22-0
• Molecular Formula: C₃₃H₄₄O₆Si
• Molecular Weight: 564.794
• Mol file: 153718-22-0.mol

Synonyms:2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside

There total 8 articles about 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside 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:

Acetic acid (3R,4S,5S,6R)-2,3,5-triacetoxy-6-((R)-1-allyloxy-ethyl)-tetrahydro-pyran-4-yl ester (176589-70-1) → 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside (153718-22-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) acetic acid, hydrazine, 2.) Vilsmeier bromide, s-collidine / 1.) DMF, 50 deg C, 2 h, 2.) CH₂Cl₂, 2 h

2: silver trifluoromethanesulfonate, s-collidine / CH₂Cl₂ / 1 h / -28 °C

3: 1.) sodium methoxide, 2.) sodium hydride / 1.) methanol, RT, 2 h, 2.) DMF, 2 h

4: 1.) a) 1,5-cyclooctadienebis(diphenylmethylphosphine)iridium hexafluorophosphate, hydrogen, 2.) lithium bromide, H⁺ resin / 1.) a) THF, 20 min, b) THF, 16 h, 2.) 90percent aq. acetonitrile, 15 min

With 2,4,6-trimethyl-pyridine; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; H⁺ resin; Vilsmeier bromide; hydrogen; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; acetic acid; lithium bromide; hydrazine; In dichloromethane;

DOI:10.1021/ja00084a003

Reference yield:

(3R,4S,5R,6S)-6-((R)-1-Allyloxy-ethyl)-tetrahydro-pyran-2,3,4,5-tetraol → 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside (153718-22-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 4-(N,N-dimethylamino)pyridine, pyridine / 16 h

2: 1.) acetic acid, hydrazine, 2.) Vilsmeier bromide, s-collidine / 1.) DMF, 50 deg C, 2 h, 2.) CH₂Cl₂, 2 h

3: silver trifluoromethanesulfonate, s-collidine / CH₂Cl₂ / 1 h / -28 °C

4: 1.) sodium methoxide, 2.) sodium hydride / 1.) methanol, RT, 2 h, 2.) DMF, 2 h

5: 1.) a) 1,5-cyclooctadienebis(diphenylmethylphosphine)iridium hexafluorophosphate, hydrogen, 2.) lithium bromide, H⁺ resin / 1.) a) THF, 20 min, b) THF, 16 h, 2.) 90percent aq. acetonitrile, 15 min

With pyridine; 2,4,6-trimethyl-pyridine; dmap; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; H⁺ resin; Vilsmeier bromide; hydrogen; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; acetic acid; lithium bromide; hydrazine; In dichloromethane;

DOI:10.1021/ja00084a003

Reference yield:

2-(trimethylsilyl)ethyl 6-O-allyl-2,3,4-tri-O-acetyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside (153718-19-5) → 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside (153718-22-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) sodium methoxide, 2.) sodium hydride / 1.) methanol, RT, 2 h, 2.) DMF, 2 h

2: 1.) a) 1,5-cyclooctadienebis(diphenylmethylphosphine)iridium hexafluorophosphate, hydrogen, 2.) lithium bromide, H⁺ resin / 1.) a) THF, 20 min, b) THF, 16 h, 2.) 90percent aq. acetonitrile, 15 min

With (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; H⁺ resin; hydrogen; sodium methylate; sodium hydride; lithium bromide;

DOI:10.1021/ja00084a003

upstream raw materials:

2-(trimethylsilyl)ethyl 6-O-allyl-2,3,4-tri-O-benzyl-7-deoxy-β-D-glycero-D-galacto-heptopyranoside

benzyl bromide

(2S,3R,4S,5R,6R)-2-((R)-1-Allyloxy-ethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,4,5-triol

6-O-allyl-7-deoxy-1,2;3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptopyranose

Downstream raw materials:

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-{(R)-1-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-yl]-ethoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester

Refernces