benzoic acid 6-(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: benzoic acid 6-(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 931098-49-6
• Molecular Formula: C₅₂H₅₈O₁₂
• Molecular Weight: 875.025
• Mol file: 931098-49-6.mol

Synonyms:benzoic acid 6-(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property of benzoic acid 6-(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzoic acid 6-(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester

There total 12 articles about benzoic acid 6-(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester 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%

benzoic acid 6-(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester → benzoic acid 5-benzyloxy-2-benzyloxymethyl-6-hydroxy-4-methoxy-tetrahydro-pyran-3-yl ester + benzoic acid 6-(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester (931098-49-6) + allyl 2,6-dibenzyl-3-methyl-α-D-mannopyranoside (187732-08-7)

Guidance literature:

With silver perchlorate; tin(IV) chloride; In diethyl ether; at 0 ℃; for 36h;

DOI:10.1021/jo061991n

Reference yield: 76.0%

(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-trimethyl-silane (931098-45-2) + phthalic acid 1-(5-benzoyloxy-3-benzyloxy-6-benzyloxymethyl-4-methoxy-tetrahydro-pyran-2-yl) ester 2-methyl ester → benzoic acid 6-(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester + benzoic acid 6-(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester (931098-49-6)

Guidance literature:

With silver perchlorate; tin(IV) chloride; In diethyl ether; at 0 ℃; for 36h;

DOI:10.1021/jo061991n

Reference yield:

D-Mannose (530-26-7) → benzoic acid 6-(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester (931098-49-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 80 percent / Sc(OTf)3 / 6 h / Heating

2.1: 83 percent / fluoroboric acid / diethyl ether; dimethylformamide

3.1: n-Bu₂SnO / methanol / Heating

3.2: 30.6 g / dimethylformamide / 50 °C

4.1: 66 percent / NaH; imidazole / tetrahydrofuran; dimethylformamide / 1 h

5.1: 73 percent / NaBH₃CN; TiCl₄ / acetonitrile / 3 h / 0 °C

6.1: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h

7.1: SnCl₄; AgClO₄ / diethyl ether / 36 h / 0 °C

8.1: 78 percent / SnCl₄; AgClO₄ / diethyl ether / 36 h / 0 °C

With 1H-imidazole; tetrafluoroboric acid; silver perchlorate; titanium tetrachloride; tin(IV) chloride; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; triethylamine; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 7.1: Mukaiyama glycosidation;

DOI:10.1021/jo061991n

upstream raw materials:

(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-trimethyl-silane

6-allyloxy-7-benzyloxy-8-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

benzoic acid 6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester

D-Mannose

Downstream raw materials:

(2R,3R,4S,5S,6R)-6-((2R,3R,4S,5S,6S)-6-Allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-ol

[6-(6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy]-trimethyl-silane