methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-(phenylsulfonyl)-β-D-erythro-hex-2-enopyranoside

Base Information

• Chemical Name: methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-(phenylsulfonyl)-β-D-erythro-hex-2-enopyranoside
• CAS No.: 273921-08-7
• Molecular Formula: C₂₀H₂₀O₆S
• Molecular Weight: 388.441
• Mol file: 273921-08-7.mol

Synonyms:methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-(phenylsulfonyl)-β-D-erythro-hex-2-enopyranoside

Chemical Property of methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-(phenylsulfonyl)-β-D-erythro-hex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-(phenylsulfonyl)-β-D-erythro-hex-2-enopyranoside

There total 12 articles about methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-(phenylsulfonyl)-β-D-erythro-hex-2-enopyranoside 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:

Methanesulfonic acid (2R,4aR,6R,7S,8S,8aR)-8-benzenesulfonyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester → methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-(phenylsulfonyl)-β-D-erythro-hex-2-enopyranoside (273921-08-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1055/s-2002-32960

Reference yield:

Methanesulfonic acid (2R,4aR,6R,7R,8R,8aR)-8-benzenesulfonyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (1053662-98-8) → methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-(phenylsulfonyl)-β-D-erythro-hex-2-enopyranoside (273921-08-7)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In diethyl ether; dichloromethane; at -20 - 20 ℃; for 1h;

DOI:10.1016/S0957-4166(99)00519-4

Reference yield:

thiophenol (108-98-5) → methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-(phenylsulfonyl)-β-D-erythro-hex-2-enopyranoside (273921-08-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / 1,1,3,3-tetramethylguanidine / dimethylformamide / 2.5 h / 80 - 90 °C

2: 100 percent / magnesium monoperoxyphthalate / methanol / 2.5 h / 20 °C

3: pyridine / 4 °C

4: 7.55 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.08 h

With magnesium monoperoxyphthalate hexahydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N,N',N'-tetramethylguanidine; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Addition / 2: Oxidation / 3: mesylation / 4: Elimination;

DOI:10.1021/jo991380d

upstream raw materials:

Methanesulfonic acid (2R,4aR,6R,7R,8R,8aR)-8-benzenesulfonyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

1,2:5,6-di-O-isopropylidene-3-O-(methylsulphonyl)-α-D-allofuranose

thiophenol

3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-phenylsulfanyl-α-D-glucofuranose

Downstream raw materials:

2-((2R,3S,4R,5R,6R)-4-Benzenesulfonyl-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-malonic acid dimethyl ester

2-((2R,4aR,6R,7S,8R,8aR)-8-Benzenesulfonyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-malonic acid dimethyl ester

methyl 2,3-dideoxy-2-N-morpholino-4,6-O-(phenylmethylene)-3-C-phenylsulfonyl-β-D-glucopyranoside

methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-C-phenylsulfonyl-2-N-pyrrolidino-β-D-glucopyranoside