(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

Base Information

• Chemical Name: (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
• CAS No.: 194594-71-3
• Molecular Formula: C₄₅H₅₄O₁₁
• Molecular Weight: 770.917
• Mol file: 194594-71-3.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 15 articles about (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 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: 93.0%

allyl 4-acetyl-2,6-dibenzyl-3-methyl-α-D-mannopyranosyl-(1->4)-2,6-dibenzyl-3-methyl-α-D-mannopyranoside (187732-19-0) → (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 (194594-71-3)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; for 2h; Ambient temperature;

DOI:10.1080/07328309708006545

Reference yield: 92.0%

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 (931098-49-6) → (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 (194594-71-3)

Guidance literature:

With sodium hydroxide; In methanol; for 3.5h;

DOI:10.1021/jo061991n

Reference yield:

D-Mannose (530-26-7) → (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 (194594-71-3)

Guidance literature:

Multi-step reaction with 9 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

9.1: 92 percent / NaOH / methanol / 3.5 h

With 1H-imidazole; sodium hydroxide; 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:

allyl 4-acetyl-2,6-dibenzyl-3-methyl-α-D-mannopyranosyl-(1->4)-2,6-dibenzyl-3-methyl-α-D-mannopyranoside

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

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

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

Downstream raw materials:

allyl O-(4-O-acetyl-2,6-di-O-benzyl-3-O-methyl-α-D-mannopyranosyl)-[(1->4)-O-(2,6-di-O-benzyl-3-O-methyl-α-D-mannopyranosyl)]2-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-mannopyranoside

allyl O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-[(1->4)-O-(2,6-di-O-benzyl-3-O-methyl-α-D-mannopyranosyl)]2-(1->4)-2,6-di-O-benzyl-3-O-methyl-α-D-mannopyranoside

[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