(1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-2-phenyl-1,3-dioxane

Base Information

• Chemical Name: (1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-2-phenyl-1,3-dioxane
• CAS No.: 172967-72-5
• Molecular Formula: C₃₁H₃₄O₇
• Molecular Weight: 518.607

Synonyms:(1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-2-phenyl-1,3-dioxane

Chemical Property of (1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-2-phenyl-1,3-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-2-phenyl-1,3-dioxane

There total 12 articles about (1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-2-phenyl-1,3-dioxane 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: 94.0%

acetic anhydride (108-24-7) + (1'R,2R,2'R,4R,5S)-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-5-hydroxy-2-phenyl-1,3-dioxane (168254-34-0) → (1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-2-phenyl-1,3-dioxane (172967-72-5)

Guidance literature:

With pyridine;

DOI:10.1016/0040-4039(94)02458-N

Reference yield:

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,121524-01-4,121570-34-1,108032-93-5) → (1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-2-phenyl-1,3-dioxane (172967-72-5)

Guidance literature:

Multi-step reaction with 9 steps

1: NH₃ / methanol / Ambient temperature

2: HBF₄*OEt₂ / dimethylformamide / Ambient temperature

3: 1.) n-Bu₂SnO, 2.) CsF / 1.) toluene, reflux, 3 h, 2.) DMF, room temperature, 12 h

4: 94 percent / NaH / dimethylformamide; paraffin / 12 h / Ambient temperature

5: 54 percent / NBS / acetone; H₂O / 0.5 h / Ambient temperature

6: 66 percent / n-BuLi / tetrahydrofuran; hexane / -78 deg C -> room temperature

7: 2.32 g / (COCl)2, DMSO, Et₃N / CH₂Cl₂

8: L-Selectride / tetrahydrofuran

9: 94 percent / pyridine / 6 h / Ambient temperature

With tetrafluoroboric acid diethyl ether; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; ammonia; L-Selectride; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; cesium fluoride; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; paraffin;

DOI:10.1016/S0040-4020(97)00360-8

Reference yield:

(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-63-1,105088-17-3,149495-84-1,77481-62-0) → (1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-2-phenyl-1,3-dioxane (172967-72-5)

Guidance literature:

Multi-step reaction with 8 steps

1: HBF₄*OEt₂ / dimethylformamide / Ambient temperature

2: 1.) n-Bu₂SnO, 2.) CsF / 1.) toluene, reflux, 3 h, 2.) DMF, room temperature, 12 h

3: 94 percent / NaH / dimethylformamide; paraffin / 12 h / Ambient temperature

4: 54 percent / NBS / acetone; H₂O / 0.5 h / Ambient temperature

5: 66 percent / n-BuLi / tetrahydrofuran; hexane / -78 deg C -> room temperature

6: 2.32 g / (COCl)2, DMSO, Et₃N / CH₂Cl₂

7: L-Selectride / tetrahydrofuran

8: 94 percent / pyridine / 6 h / Ambient temperature

With tetrafluoroboric acid diethyl ether; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; L-Selectride; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; cesium fluoride; In tetrahydrofuran; pyridine; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; paraffin;

DOI:10.1016/S0040-4020(97)00360-8

upstream raw materials:

acetic anhydride

(1'R,2R,2'R,4R,5S)-4-<1-benzyloxy-2-(4-methoxybenzyl)oxy-3-butenyl>-5-hydroxy-2-phenyl-1,3-dioxane

benzaldehyde dimethyl acetal

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside

Downstream raw materials:

(1'R,2R,2'R,4R,5S)-5-acetoxy-4-<1-benzyloxy-2-hydroxy-3-butenyl>-2-phenyl-1,3-dioxane

(1'R,2R,2'R,4R,5S)-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-5-hydroxy-2-phenyl-1,3-dioxane

(1'R,2R,2'R,4R,5S)-5-acetoxy-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-2-phenyl-1,3-dioxane

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