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

Base Information

• Chemical Name: (4aR,6R,7R,8S,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS No.: 129031-01-2
• Molecular Formula: C₄₈H₅₂O₁₀
• Molecular Weight: 788.935
• Mol file: 129031-01-2.mol

Synonyms:

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

There total 7 articles about (4aR,6R,7R,8S,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-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: 46.0%

2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl bromide (59055-61-7) + methyl 3-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside (2774-19-8,14419-69-3,15887-67-9,23392-28-1,57539-08-9,61277-63-2,65877-21-6,74410-51-8,76419-48-2,80734-73-2,86363-44-2,89301-79-1,94061-92-4,108739-92-0,129706-93-0,143005-12-3,94062-87-0) → methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-β-L-rhamnopyranosyl)-β-D-galactopyranoside (129031-01-2)

Guidance literature:

With 4 A molecular sieve; silver carbonate; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1016/0008-6215(90)84132-E

Reference yield: 37.0%

methyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (129706-93-0) + ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside (131545-02-3,116391-11-8) → (4aR,6R,7R,8S,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine (127753-87-1,129031-01-2,129031-03-4)

Guidance literature:

With molecular sieve; methyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.75h;

DOI:10.1039/P19880002729

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-β-L-rhamnopyranosyl)-β-D-galactopyranoside (129031-01-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / toluene-p-sulfonic acid / dimethylformamide / 1.5 h / 70 °C / 12 Torr

2: 46 percent / Ag₂CO₃, molecular sieve 4 Angstroem / CH₂Cl₂ / 20 h / Ambient temperature

With 4 A molecular sieve; toluene-4-sulfonic acid; silver carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(90)84132-E

upstream raw materials:

2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl bromide

methyl 3-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

benzaldehyde dimethyl acetal

ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamanopyranoside

Downstream raw materials:

methyl 2-O-β-L-rhamnopyranosyl-β-D-galactopyranoside