(2S,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid

Base Information

• Chemical Name: (2S,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid
• CAS No.: 177018-19-8
• Molecular Formula: C₆₈H₇₀O₁₂
• Molecular Weight: 1079.3
• Mol file: 177018-19-8.mol

Synonyms:

Chemical Property of (2S,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid

There total 3 articles about (2S,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid 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:

(2S,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexanal → (2S,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid (177018-19-8)

Guidance literature:

With sodium chlorite; aminosulfonic acid; In 1,4-dioxane; water; for 1h; Yield given;

DOI:10.1016/0040-4039(96)00316-4

Reference yield:

(2R,3R,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexan-1-ol → (2S,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid (177018-19-8)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

2: sodium chlorite, H₂NSO₃H / dioxane; H₂O / 1 h

With sodium chlorite; oxalyl dichloride; aminosulfonic acid; dimethyl sulfoxide; triethylamine; In 1,4-dioxane; dichloromethane; water;

DOI:10.1016/0040-4039(96)00316-4

Reference yield:

2,3,4,6-tetra-O-benzyl-D-mannopyranose (4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5) → (2S,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexanoic acid (177018-19-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent

2: 1.) NIS, TfOH, 2.) TBAF, 3.) oxalyl chloride, DMSO, 4.) sodium chlorite / 1.) EtOAc, Ch₂Cl₂, -40 deg C, 1.5 h

With sodium chlorite; N-iodo-succinimide; oxalyl dichloride; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; dimethyl sulfoxide;

DOI:10.7164/antibiotics.49.713

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-mannopyranose