Phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: Phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 141342-85-0
• Molecular Formula: C₆₈H₇₁NO₁₉S
• Molecular Weight: 1238.37

Synonyms:Phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of Phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 6 articles about Phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-6-O-benzyl-2-deoxy-2-phthalimido-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: 90.0%

(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran (107802-80-2) + Phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (141342-84-9) → Phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (141342-85-0)

Guidance literature:

With 4 A molecular sieve; tetrabutylammomium bromide; copper(ll) bromide; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; for 96h; Ambient temperature;

DOI:10.1016/0008-6215(92)84057-Y

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → Phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (141342-85-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 69.5 percent / trimethylsilyl triflate / CH₂Cl₂ / 72 h / Ambient temperature

2: 1.) NaOCH₃; 2.) 4-toluenesulfonic acid monohydrate / 1.) methanol, r.t., 3 h; 2.) r.t., 16 h

3: 84.9 percent / NaCNBH₃, 3 Angstroem mol. sieves, etheric HCl / tetrahydrofuran / 0.33 h / 0 °C

4: 64 percent / a) 4 Angstr_. mol. sieves, b) SnCl₂, silver trifluoromethanesulfonate / CH₂Cl₂; toluene / a) -15 deg C, 0.5 h, b) -15 deg C to r.t., 2 h

5: 90 percent / 4 Angstroem mol. sieves, Bu₄NBr, CuBr₂ / dimethylformamide; 1,2-dichloro-ethane / 96 h / Ambient temperature

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; p-toluenesulfonic acid monohydrate; tetrabutylammomium bromide; sodium methylate; silver trifluoromethanesulfonate; sodium cyanoborohydride; tin(ll) chloride; copper(ll) bromide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0008-6215(92)84057-Y

Reference yield:

phenylthiotrimethylsilane (4551-15-9) → Phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (141342-85-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 69.5 percent / trimethylsilyl triflate / CH₂Cl₂ / 72 h / Ambient temperature

2: 1.) NaOCH₃; 2.) 4-toluenesulfonic acid monohydrate / 1.) methanol, r.t., 3 h; 2.) r.t., 16 h

3: 84.9 percent / NaCNBH₃, 3 Angstroem mol. sieves, etheric HCl / tetrahydrofuran / 0.33 h / 0 °C

4: 64 percent / a) 4 Angstr_. mol. sieves, b) SnCl₂, silver trifluoromethanesulfonate / CH₂Cl₂; toluene / a) -15 deg C, 0.5 h, b) -15 deg C to r.t., 2 h

5: 90 percent / 4 Angstroem mol. sieves, Bu₄NBr, CuBr₂ / dimethylformamide; 1,2-dichloro-ethane / 96 h / Ambient temperature

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; p-toluenesulfonic acid monohydrate; tetrabutylammomium bromide; sodium methylate; silver trifluoromethanesulfonate; sodium cyanoborohydride; tin(ll) chloride; copper(ll) bromide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0008-6215(92)84057-Y

upstream raw materials:

(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran

Phenyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

phenylthiotrimethylsilane

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