(4aR,6R,7R,8S,8aS)-7-[(2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

• Chemical Name: (4aR,6R,7R,8S,8aS)-7-[(2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS No.: 208662-05-9
• Molecular Formula: C₇₉H₁₁₄O₁₂
• Molecular Weight: 1255.77
• Mol file: 208662-05-9.mol

Synonyms:(4aR,6R,7R,8S,8aS)-7-[(2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property of (4aR,6R,7R,8S,8aS)-7-[(2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6R,7R,8S,8aS)-7-[(2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 8 articles about (4aR,6R,7R,8S,8aS)-7-[(2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 78.0%

phenyl 2,4-di-O-benzyl-3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside (190443-02-8) + (4aR,6R,7R,8R,8aS)-8-(4-Methoxy-benzyloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (208661-97-6) → (4aR,6R,7R,8S,8aS)-7-[(2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine (208662-05-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; MS-4 Angstroem; In toluene; at -20 ℃; for 1h;

DOI:10.1080/07328309808002905

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (4aR,6R,7R,8S,8aS)-7-[(2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine (208662-05-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / H₂SO₄ / tetrahydrofuran / 20 h / Ambient temperature

2: 1.) Bu₂SnO, 2.) tetra n-butyl ammonium iodide / 1) toluene, reflux, 24 h; 2) THF, reflux, 24 h

3: 78 percent / MS-4 Angstroem, N-iodosuccinimide, trifluoromethanesulfonic acid / toluene / 1 h / -20 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; MS-4 Angstroem; sulfuric acid; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; In tetrahydrofuran; toluene;

DOI:10.1080/07328309808002905

Reference yield:

benzyl bromide (100-39-0) → (4aR,6R,7R,8S,8aS)-7-[(2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine (208662-05-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1) DMF, 0 deg C, 30 min; 2) DMF, 2 h

2: 78 percent / MS-4 Angstroem, N-iodosuccinimide, trifluoromethanesulfonic acid / toluene / 1 h / -20 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; MS-4 Angstroem; sodium hydride; In toluene;

DOI:10.1080/07328309808002905

upstream raw materials:

phenyl 2,4-di-O-benzyl-3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside

(4aR,6R,7R,8R,8aS)-8-(4-Methoxy-benzyloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

benzaldehyde dimethyl acetal

benzyl bromide

Downstream raw materials:

(4aR,6R,7R,8S,8aR)-7-((2S,3S,4R,5S,6S)-3,5-Bis-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-6-(2-tetradecyl-hexadecyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol