ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
• CAS No.: 289057-14-3
• Molecular Formula: C₅₇H₇₁ClO₁₁SSi
• Molecular Weight: 1027.79
• Mol file: 289057-14-3.mol

Synonyms:ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Chemical Property of ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

There total 7 articles about ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 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: 79.0%

ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (289057-12-1) + Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-bromo-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester (289057-13-2) → ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (289057-14-3)

Guidance literature:

With 2,3,5-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; toluene; at -30 ℃; for 0.333333h;

DOI:10.1016/S0040-4020(00)00239-8

Reference yield:

benzyl bromide (100-39-0) → ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (289057-14-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / NaH / dimethylformamide / 0.25 h

2: 85 percent / BH₃*Me₃N; AlCl₃; 4 Angstroem molecular sieves / CH₂Cl₂; diethyl ether / 0.17 h

3: NaH / dimethylformamide / 0.25 h

4: 1.896 g / BF₃*Et₂O / CHCl₃ / 1.5 h / 45 °C

5: 79 percent / AgOTf; collidine; 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 0.33 h / -30 °C

With 2,3,5-trimethyl-pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; boron trifluoride diethyl etherate; silver trifluoromethanesulfonate; sodium hydride; In diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: Reduction / 3: Etherification / 4: desilylation / 5: Condensation;

DOI:10.1016/S0040-4020(00)00239-8

Reference yield:

ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside (153185-20-7) → ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (289057-14-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / NaH / dimethylformamide / 0.25 h

2: 85 percent / BH₃*Me₃N; AlCl₃; 4 Angstroem molecular sieves / CH₂Cl₂; diethyl ether / 0.17 h

3: NaH / dimethylformamide / 0.25 h

4: 1.896 g / BF₃*Et₂O / CHCl₃ / 1.5 h / 45 °C

5: 79 percent / AgOTf; collidine; 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 0.33 h / -30 °C

With 2,3,5-trimethyl-pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; boron trifluoride diethyl etherate; silver trifluoromethanesulfonate; sodium hydride; In diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: Reduction / 3: Etherification / 4: desilylation / 5: Condensation;

DOI:10.1016/S0040-4020(00)00239-8

upstream raw materials:

ethyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-bromo-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

benzyl bromide

ethyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside