(2R,3R,4S,5R,6R)-2-Ethylsulfanyl-6-hydroxymethyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,5-diol

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-2-Ethylsulfanyl-6-hydroxymethyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,5-diol
• CAS No.: 173676-16-9
• Molecular Formula: C₄₂H₅₀O₁₀S
• Molecular Weight: 746.919

Synonyms:

Chemical Property of (2R,3R,4S,5R,6R)-2-Ethylsulfanyl-6-hydroxymethyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6R)-2-Ethylsulfanyl-6-hydroxymethyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,5-diol

There total 3 articles about (2R,3R,4S,5R,6R)-2-Ethylsulfanyl-6-hydroxymethyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,5-diol 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: 20.6%

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside (64694-21-9) + ethanethiol (75-08-1) → (2S,3R,4S,5R,6R)-2-Ethylsulfanyl-6-hydroxymethyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,5-diol (173676-15-8) + (2R,3R,4S,5R,6R)-2-Ethylsulfanyl-6-hydroxymethyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,5-diol (173676-16-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 5 ℃; for 4h;

DOI:10.1016/0008-6215(95)00231-X

Reference yield:

1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (74666-83-4,105990-37-2,125354-46-3,125354-47-4,125411-99-6,108739-67-9) → (2R,3R,4S,5R,6R)-2-Ethylsulfanyl-6-hydroxymethyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,5-diol (173676-16-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / CuBr₂, Bu₄NBr, 4A molecular sieves / 1,2-dichloro-ethane; dimethylformamide / 72 h / 24 °C

2: 20.6 percent / BF₃*Et₂O / CH₂Cl₂ / 4 h / 0 - 5 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(95)00231-X

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → (2R,3R,4S,5R,6R)-2-Ethylsulfanyl-6-hydroxymethyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,5-diol (173676-16-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / CuBr₂, Bu₄NBr, 4A molecular sieves / 1,2-dichloro-ethane; dimethylformamide / 72 h / 24 °C

2: 20.6 percent / BF₃*Et₂O / CH₂Cl₂ / 4 h / 0 - 5 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(95)00231-X

upstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside

ethanethiol

1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

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