3-O-carboxymethyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

Base Information

• Chemical Name: 3-O-carboxymethyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
• CAS No.: 1054636-52-0
• Molecular Formula: C₄₃H₅₀O₁₂
• Molecular Weight: 758.863
• Mol file: 1054636-52-0.mol

Synonyms:3-O-carboxymethyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

Chemical Property of 3-O-carboxymethyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-carboxymethyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

There total 5 articles about 3-O-carboxymethyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-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: 57.0%

bromoacetic acid methyl ester (96-32-2) + 6-O-tert-butyldiphenylsilyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside (270922-33-3) → 3-O-carboxymethyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside (1054636-52-0)

Guidance literature:

6-O-tert-butyldiphenylsilyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside; With di(n-butyl)tin oxide; In toluene; for 1h; Heating;

bromoacetic acid methyl ester; With tetra-(n-butyl)ammonium iodide; In toluene; for 1h; Heating;

With sodium hydroxide; In ethanol; for 1h; Further stages.;

DOI:10.1021/jo991898h

Reference yield:

3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside (224325-01-3) → 3-O-carboxymethyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside (1054636-52-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 63 percent / aq. HCl / diethyl ether; methanol / 0.33 h / 20 °C

2.1: dibutyltin oxide / toluene / 1 h / Heating

2.2: n-Bu₄NI / toluene / 1 h / Heating

2.3: 57 percent / aq. NaOH / ethanol / 1 h

With hydrogenchloride; di(n-butyl)tin oxide; In methanol; diethyl ether; toluene; 1.1: Hydrolysis / 2.1: Cyclization / 2.2: Alkylation / 2.3: Hydrolysis;

DOI:10.1021/jo991898h

Reference yield:

((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid (R)-2-(tert-butyl-diphenyl-silanyloxy)-1-((4S,5R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethyl ester → 3-O-carboxymethyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside (1054636-52-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 88 percent / pyridine / toluene; tetrahydrofuran / 1 h / -78 °C

2.1: 88 percent / methyl triflate; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 18 h / 20 °C

3.1: 83 percent / BH₃*Me₂S / CH₂Cl₂; tetrahydrofuran / 0 - 20 °C

4.1: 63 percent / aq. HCl / diethyl ether; methanol / 0.33 h / 20 °C

5.1: dibutyltin oxide / toluene / 1 h / Heating

5.2: n-Bu₄NI / toluene / 1 h / Heating

5.3: 57 percent / aq. NaOH / ethanol / 1 h

With pyridine; hydrogenchloride; 2,6-di-tert-butyl-4-methylpyridine; dimethylsulfide borane complex; 4 A molecular sieve; di(n-butyl)tin oxide; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 1.1: methylenation / 2.1: Cyclization / 3.1: Reduction / 4.1: Hydrolysis / 5.1: Cyclization / 5.2: Alkylation / 5.3: Hydrolysis;

DOI:10.1021/jo991898h

upstream raw materials:

bromoacetic acid methyl ester

6-O-tert-butyldiphenylsilyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-deoxy-D-arabino-hex-1-enopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-β-D-galactopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside