Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-allyloxy-6-((2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Base Information

Chemical Name:Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-allyloxy-6-((2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
CAS No.:640722-60-7
Molecular Formula:C₃₆H₄₂O₁₅
Molecular Weight:714.72
Hs Code.:

Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-allyloxy-6-((2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Synonyms:Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-allyloxy-6-((2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

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Chemical Property of Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-allyloxy-6-((2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

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Technology Process of Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-allyloxy-6-((2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

There total 8 articles about Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-allyloxy-6-((2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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: 85.0%

: 92008-11-2
2,4,6-Tri-O-acetyl-β-methyl-D-glucopyranoside

: 3-O-allyl-2-O-benzoyl-4,6-O-benzylidene-D-glucopyranosyl trichloroacetimidate

: 640722-60-7
Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-allyloxy-6-((2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 - 20 ℃; for 3h;
DOI:10.1016/j.carres.2003.08.004

Reference yield:

: 91109-44-3
3-O-allyl-D-glucopyranose

: 640722-60-7
Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-allyloxy-6-((2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: triethyl orthoformate; TSA / dimethylformamide / 20 °C

2: pyridine / 4 h / 20 °C

3: NH₃ / toluene; methanol / 20 °C

4: 4.07 g / DBU / CH₂Cl₂ / 3 h / 20 °C

5: 85 percent / TMSOTf / CH₂Cl₂ / 3 h / -20 - 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; orthoformic acid triethyl ester; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.carres.2003.08.004

Reference yield:

: 100-52-7
benzaldehyde

: 640722-60-7
Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-allyloxy-6-((2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: triethyl orthoformate; TSA / dimethylformamide / 20 °C

2: pyridine / 4 h / 20 °C

3: NH₃ / toluene; methanol / 20 °C

4: 4.07 g / DBU / CH₂Cl₂ / 3 h / 20 °C

5: 85 percent / TMSOTf / CH₂Cl₂ / 3 h / -20 - 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; orthoformic acid triethyl ester; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.carres.2003.08.004