ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside
• CAS No.: 123212-53-3
• Molecular Formula: C₃₀H₂₉NO₆S
• Molecular Weight: 531.629
• Mol file: 123212-53-3.mol

Synonyms:ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside

Chemical Property:

• Boiling Point: 683.0±55.0 °C(Predicted)
• Density: 1.36±0.1 g/cm3(Predicted)

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl3-O-benyl-4,6-O-[(R)-phenylmethylene]-1-thio-a-D-Mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Ethyl 3-O-benyl-4,6-O-[(R)-phenylmethylene]-1-thio-a-D-Mannopyranoside has been used to prepare L-Galactosylated dimeric sialyl Lewis X structures.

Technology Process of ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside

There total 19 articles about ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside 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: 91.0%

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3) + benzyl bromide (100-39-0) → ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside (123212-53-3)

Guidance literature:

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 20 ℃; for 3.5h; Inert atmosphere;

DOI:10.1021/ja4056678

Reference yield: 51.0%

(ethylthio)trimethylsilane (5573-62-6) + 1-O-Acetyl-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranose (144221-80-7) → Ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-allopyranoside (123212-53-3,129519-27-3,144300-02-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1002/hlca.19920750505

Reference yield:

phthalic anhydride (85-44-9) → Ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-allopyranoside (123212-53-3,129519-27-3,144300-02-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / Et₃N / methanol / 0.5 h / Ambient temperature

2: 44 percent / NaH / dimethylformamide / 24 h / Ambient temperature

3: 1 M aq. NaOH / dioxane / 5 h / Ambient temperature

4: Ac₂O, pyridine / 48 h / Ambient temperature

5: hydrogen / 2)2>PF₆ / tetrahydrofuran / 3 h / Ambient temperature

6: water, HgO, HgCl₂ / acetone / 1 h / Ambient temperature

7: 97 percent / pyridine / 12 h / Ambient temperature

8: 51 percent / 4-Angstroem molecular sieves, trimethylsilyl triflate / CH₂Cl₂ / 12 h / Ambient temperature

With pyridine; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; water; hydrogen; acetic anhydride; sodium hydride; triethylamine; mercury dichloride; mercury(II) oxide; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/hlca.19920750505

upstream raw materials:

(ethylthio)trimethylsilane

1-O-Acetyl-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranose

phthalic anhydride

Allyl 2-Amino-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside

Downstream raw materials:

ethyl 6-O-benzoyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

methyl 2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

methyl 2-amino-2-deoxy-β-D-glucopyranosyl-(1->4)-2-amino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside