ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• CAS No.: 851625-41-7
• Molecular Formula: C₁₉H₂₄O₇S
• Molecular Weight: 396.461
• Mol file: 851625-41-7.mol

Synonyms:ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Chemical Property of ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

There total 1 articles about ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-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: 72.0%

ethyl 1-thio-α-D-mannopyranoside (7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3) + benzaldehyde dimethyl acetal (1125-88-8) + acetic anhydride (108-24-7) → ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (851625-41-7)

Guidance literature:

ethyl 1-thio-α-D-mannopyranoside; benzaldehyde dimethyl acetal; With perchloric acid on silica gel; In acetonitrile; at 20 ℃;

acetic anhydride; With methanol; perchloric acid on silica gel; In acetonitrile; at 20 ℃;

DOI:10.1016/j.carres.2005.02.012

Reference yield:

ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (851625-41-7) → ethyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzyl-1-thio-α-D-mannopyranoside (876406-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 83 percent / sodium cyanoborohydride; hydrogen chloride / tetrahydrofuran; diethyl ether / 0.5 h

2.1: molecular sieves 4 Angstroem; triethylsilyl trifluoromethanesulfonate / diethyl ether / 0.25 h / -20 °C

2.2: 82 percent / diethyl ether / 0.5 h / -20 °C

With hydrogenchloride; 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether;

Reference yield:

ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (851625-41-7) → 4,5-bis-benzyloxy-3-[6-benzyloxymethyl-3,4-dihydroxy-5-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (876406-43-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 83 percent / sodium cyanoborohydride; hydrogen chloride / tetrahydrofuran; diethyl ether / 0.5 h

2.1: molecular sieves 4 Angstroem; triethylsilyl trifluoromethanesulfonate / diethyl ether / 0.25 h / -20 °C

2.2: 82 percent / diethyl ether / 0.5 h / -20 °C

3.1: 77 percent / molecular sieves 4 Angstroem; N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 0.5 h / cooling

4.1: 80 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 6 h / 20 °C

5.1: iodobenzene diacetate; TEMPO / acetonitrile; H₂O / 3 h / 20 °C

6.1: 1.13 g / CH₂Cl₂; diethyl ether

7.1: sodium methoxide / methanol

With hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-iodo-succinimide; trifluorormethanesulfonic acid; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; sodium methylate; sodium cyanoborohydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;

upstream raw materials:

ethyl 1-thio-α-D-mannopyranoside

benzaldehyde dimethyl acetal

acetic anhydride

Downstream raw materials:

ethyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzyl-1-thio-α-D-mannopyranoside

4,5-bis-benzyloxy-3-[6-benzyloxymethyl-3,4-dihydroxy-5-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

acetic acid 3-acetoxy-6-benzyloxymethyl-2-[4,5-bis-benzyloxy-2-hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-5-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzyl-α-D-mannopyranosyl-(1->4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranosid] uronate