ethyl 2,3,4-tri-O-benzyl-6-O-(7'-trityloxyheptyl)-1-thio-α-D-galactopyranoside

Base Information

• Chemical Name: ethyl 2,3,4-tri-O-benzyl-6-O-(7'-trityloxyheptyl)-1-thio-α-D-galactopyranoside
• CAS No.: 213766-25-7
• Molecular Formula: C₅₅H₆₂O₆S
• Molecular Weight: 851.16

Synonyms:ethyl 2,3,4-tri-O-benzyl-6-O-(7'-trityloxyheptyl)-1-thio-α-D-galactopyranoside

Chemical Property of ethyl 2,3,4-tri-O-benzyl-6-O-(7'-trityloxyheptyl)-1-thio-α-D-galactopyranoside

Chemical Property:

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Technology Process of ethyl 2,3,4-tri-O-benzyl-6-O-(7'-trityloxyheptyl)-1-thio-α-D-galactopyranoside

There total 8 articles about ethyl 2,3,4-tri-O-benzyl-6-O-(7'-trityloxyheptyl)-1-thio-α-D-galactopyranoside 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%

Methanesulfonic acid 7-trityloxy-heptyl ester (213766-68-8) + ethyl 2,3,4-tri-O-benzyl-6-O-chloroacetyl-1-thio-α-D-galactopyranoside (213767-45-4) → ethyl 2,3,4-tri-O-benzyl-6-O-(7'-trityloxyheptyl)-1-thio-α-D-galactopyranoside (213766-25-7)

Guidance literature:

With sodium hydride; In tetrahydrofuran; 1.) 50 deg C, 1 h, 2.) 65 deg C, 18 h;

DOI:10.1021/jo9806097

Reference yield:

1,7-heptandiol (629-30-1) → ethyl 2,3,4-tri-O-benzyl-6-O-(7'-trityloxyheptyl)-1-thio-α-D-galactopyranoside (213766-25-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 57 percent / pyridine; CH₂Cl₂ / Ambient temperature

2: 78 percent / pyridine; CH₂Cl₂ / Ambient temperature

3: 91 percent / NaH / tetrahydrofuran / 1.) 50 deg C, 1 h, 2.) 65 deg C, 18 h

With sodium hydride; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jo9806097

Reference yield:

benzyl bromide (100-39-0) → ethyl 2,3,4-tri-O-benzyl-6-O-(7'-trityloxyheptyl)-1-thio-α-D-galactopyranoside (213766-25-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) 0 deg C to room temperature, overnight

2: 95 percent / TBAF / tetrahydrofuran / 6 h / Ambient temperature

3: 91 percent / NaH / tetrahydrofuran / 1.) 50 deg C, 1 h, 2.) 65 deg C, 18 h

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo9806097

upstream raw materials:

Methanesulfonic acid 7-trityloxy-heptyl ester

ethyl 2,3,4-tri-O-benzyl-6-O-chloroacetyl-1-thio-α-D-galactopyranoside

1,7-heptandiol

benzyl bromide

Downstream raw materials:

(1S,3R,4R,5S,6S,7R,19R,21S,22S,23R)-4,5,6,23-Tetrakis-benzyloxy-22-((2R,3R,5R,6R)-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-21-methoxy-2,9,17,20,24-pentaoxa-tricyclo[17.2.2.1^3,7]tetracosane

methyl 3-O-allyl-2-O-[2',3',4'-tri-O-benzyl-6'-O-(7''-hydroxyheptyl)-α-D-galactopyranosyl]-4-O-benzyl-6-O-methanesulfonyl-α-D-mannopyranoside

methyl 2-O-(3'-O-allyl-4'-O-benzyl-α-D-galactopyranosyl)-2,3,4-tri-O-benzyl-6,6'-di-O-(heptane-1,7-diyl)-α-D-mannopyranoside

methyl 2-O-(2',3',4'-tri-O-benzyl-α-D-galactopyranosyl)-4-O-benzyl-6,6'-di-O-(heptane-1,7-diyl)-α-D-mannopyranoside

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