3-(hexadecylthio)-2-<(hexadecylthio)methyl>propyl 6-O-acetyl-3-deoxy-3C-methyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Base Information

• Chemical Name: 3-(hexadecylthio)-2-<(hexadecylthio)methyl>propyl 6-O-acetyl-3-deoxy-3C-methyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• CAS No.: 127542-23-8
• Molecular Formula: C₆₆H₁₁₀O₁₆S₂
• Molecular Weight: 1223.72
• Mol file: 127542-23-8.mol

Synonyms:3-(hexadecylthio)-2-<(hexadecylthio)methyl>propyl 6-O-acetyl-3-deoxy-3C-methyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Chemical Property of 3-(hexadecylthio)-2-<(hexadecylthio)methyl>propyl 6-O-acetyl-3-deoxy-3C-methyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(hexadecylthio)-2-<(hexadecylthio)methyl>propyl 6-O-acetyl-3-deoxy-3C-methyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

There total 13 articles about 3-(hexadecylthio)-2-<(hexadecylthio)methyl>propyl 6-O-acetyl-3-deoxy-3C-methyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 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: 81.0%

16-mercaptohexadecanoate (2917-26-2) + 3-bromo-2-(bromomethyl)propyl 6-O-acetyl-3-deoxy-3C-methyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (127542-22-7) → 3-(hexadecylthio)-2-<(hexadecylthio)methyl>propyl 6-O-acetyl-3-deoxy-3C-methyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (127542-23-8)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; for 3.5h; Ambient temperature;

DOI:10.1021/jo00299a044

Reference yield:

benzyl D-glucopyranoside (34246-23-6) → 3-(hexadecylthio)-2-<(hexadecylthio)methyl>propyl 6-O-acetyl-3-deoxy-3C-methyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (127542-23-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 36 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 1.25 h / Ambient temperature

2: 1. NaH 2. (p-tolylsulfonyl)imidazole / 1. mineral oil, DMF, 2 h 2. 1 h

3: 2. pyridine / 1. THF, Et₂O, 8 days heating 2. 18 h, room temperature

4: 92 percent / sodium methoxide / methanol / 20 h / Ambient temperature

5: 15.2 g / trifluoroacetic anhydride, methylsulfoxide / CH₂Cl₂ / 1.5 h / -60 °C

6: 80 percent / triethylamine / dimethylformamide / 20 h / Ambient temperature

7: 74 percent / LiAlH₄ / diethyl ether / 4 h / 0 °C

8: 64 percent / pyridine / CH₂Cl₂ / 0 deg C to room temperature

9: 79 percent / NaBH₃CN, saturated etheral hydrogen chloride, molecular sieve (3 Angstroem) / tetrahydrofuran / Ambient temperature

10: 74 percent / tetramethylurea, silver trifluoromethanesulfonate / CH₂Cl₂ / 16 h / Ambient temperature

11: 1. H₂ 2. pyridine / 1. Pd-C / 1. HOAc, 2 h 2. 2 h, room temperature

12: 75 percent / BF₃*Et₂O / CH₂Cl₂ / 12 h / Ambient temperature

13: 81 percent / cesium carbonate / dimethylformamide / 3.5 h / Ambient temperature

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; 3 A molecular sieve; NaH 2. (p-tolylsulfonyl)imidazole; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; caesium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; tetramethylurea; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00299a044

Reference yield:

benzyl 2,3-anhydro-4,6-O-benzylidene-α-D-mannpyranoside (26531-94-2,26531-97-5,35905-31-8,35905-39-6,81625-92-5) → 3-(hexadecylthio)-2-<(hexadecylthio)methyl>propyl 6-O-acetyl-3-deoxy-3C-methyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (127542-23-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 2. pyridine / 1. THF, Et₂O, 8 days heating 2. 18 h, room temperature

2: 92 percent / sodium methoxide / methanol / 20 h / Ambient temperature

3: 15.2 g / trifluoroacetic anhydride, methylsulfoxide / CH₂Cl₂ / 1.5 h / -60 °C

4: 80 percent / triethylamine / dimethylformamide / 20 h / Ambient temperature

5: 74 percent / LiAlH₄ / diethyl ether / 4 h / 0 °C

6: 64 percent / pyridine / CH₂Cl₂ / 0 deg C to room temperature

7: 79 percent / NaBH₃CN, saturated etheral hydrogen chloride, molecular sieve (3 Angstroem) / tetrahydrofuran / Ambient temperature

8: 74 percent / tetramethylurea, silver trifluoromethanesulfonate / CH₂Cl₂ / 16 h / Ambient temperature

9: 1. H₂ 2. pyridine / 1. Pd-C / 1. HOAc, 2 h 2. 2 h, room temperature

10: 75 percent / BF₃*Et₂O / CH₂Cl₂ / 12 h / Ambient temperature

11: 81 percent / cesium carbonate / dimethylformamide / 3.5 h / Ambient temperature

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; 3 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; sodium cyanoborohydride; caesium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; tetramethylurea; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00299a044

upstream raw materials:

16-mercaptohexadecanoate

3-bromo-2-(bromomethyl)propyl 6-O-acetyl-3-deoxy-3C-methyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

benzyl D-glucopyranoside

benzyl 2,3-anhydro-4,6-O-benzylidene-α-D-mannpyranoside

Downstream raw materials:

3-(hexadecylsulfonyl)-2-<(hexadecylsulfonyl)methyl>propyl 6-O-acetyl-2-O-benzoyl-3-deoxy-3-C-methyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Refernces