methyl 4,6-O-benzylidene-3-C-(cyanomethyl)-2,3-dideoxy-2-C-(2-iodoethyl)-2-C-methyl-3-C-((E)-1-propenyl)-α-D-allopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-3-C-(cyanomethyl)-2,3-dideoxy-2-C-(2-iodoethyl)-2-C-methyl-3-C-((E)-1-propenyl)-α-D-allopyranoside
• CAS No.: 122622-29-1
• Molecular Formula: C₂₂H₂₈INO₄
• Molecular Weight: 497.373

Synonyms:methyl 4,6-O-benzylidene-3-C-(cyanomethyl)-2,3-dideoxy-2-C-(2-iodoethyl)-2-C-methyl-3-C-((E)-1-propenyl)-α-D-allopyranoside

Chemical Property of methyl 4,6-O-benzylidene-3-C-(cyanomethyl)-2,3-dideoxy-2-C-(2-iodoethyl)-2-C-methyl-3-C-((E)-1-propenyl)-α-D-allopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzylidene-3-C-(cyanomethyl)-2,3-dideoxy-2-C-(2-iodoethyl)-2-C-methyl-3-C-((E)-1-propenyl)-α-D-allopyranoside

There total 16 articles about methyl 4,6-O-benzylidene-3-C-(cyanomethyl)-2,3-dideoxy-2-C-(2-iodoethyl)-2-C-methyl-3-C-((E)-1-propenyl)-α-D-allopyranoside 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:

methyl 4,6-O-benzylidene-2-deoxy-2-C-((ethoxycarbonyl)methyl)-2-C-methyl-α-D-ribo-hexopyranosid-3-ulose (122672-66-6) → methyl 4,6-O-benzylidene-3-C-(cyanomethyl)-2,3-dideoxy-2-C-(2-iodoethyl)-2-C-methyl-3-C-((E)-1-propenyl)-α-D-allopyranoside (122622-29-1)

Guidance literature:

Multi-step reaction with 15 steps

1: 2.) LiAlH₄ / 1.) THF, 15 min, 2.) THF, 0 deg C, 45 min

2: imidazole / tetrahydrofuran / 0.5 h / Ambient temperature

3: 69 percent / SOCl₂, pyridine / tetrahydrofuran / 1 h / 0 °C

4: dimethylformamide / 2 h / 100 °C

5: NaOMe / methanol / Ambient temperature

6: PCC, AcONa, Celite / CH₂Cl₂ / 0.33 h / Ambient temperature

7: tetrahydrofuran / 0.17 h

8: Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature

9: MeLi / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

10: mercuric trifluoroacetate / Ambient temperature

11: xylene / 24 h / Heating

12: hydroxylamine hydrochloride, pyridine

13: trifluoroacetic anhydride, pyridine / CH₂Cl₂ / Ambient temperature

14: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

15: iodine, triphenyl phosphine, imidazole / benzene / 0.08 h / Ambient temperature

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; thionyl chloride; Celite; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; methyllithium; iodine; sodium methylate; sodium acetate; mercury(II) trifluoroacetate; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic anhydride; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; xylene; benzene;

DOI:10.1021/jo00283a034

Reference yield:

(2R,4aR,6S,7R,8S,8aR)-7-(2-Hydroxy-ethyl)-6-methoxy-7-methyl-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (122622-39-3) → methyl 4,6-O-benzylidene-3-C-(cyanomethyl)-2,3-dideoxy-2-C-(2-iodoethyl)-2-C-methyl-3-C-((E)-1-propenyl)-α-D-allopyranoside (122622-29-1)

Guidance literature:

Multi-step reaction with 14 steps

1: imidazole / tetrahydrofuran / 0.5 h / Ambient temperature

2: 69 percent / SOCl₂, pyridine / tetrahydrofuran / 1 h / 0 °C

3: dimethylformamide / 2 h / 100 °C

4: NaOMe / methanol / Ambient temperature

5: PCC, AcONa, Celite / CH₂Cl₂ / 0.33 h / Ambient temperature

6: tetrahydrofuran / 0.17 h

7: Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature

8: MeLi / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

9: mercuric trifluoroacetate / Ambient temperature

10: xylene / 24 h / Heating

11: hydroxylamine hydrochloride, pyridine

12: trifluoroacetic anhydride, pyridine / CH₂Cl₂ / Ambient temperature

13: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

14: iodine, triphenyl phosphine, imidazole / benzene / 0.08 h / Ambient temperature

With pyridine; 1H-imidazole; thionyl chloride; Celite; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; methyllithium; iodine; sodium methylate; sodium acetate; mercury(II) trifluoroacetate; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic anhydride; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; xylene; benzene;

DOI:10.1021/jo00283a034

Reference yield:

methyl 2-deoxy-2-(2-ethoxy-2-oxoethyl)-4,6-O-(phenylmethylene)-α-D-ribohexopyranosid-3-ulose (122672-65-5) → methyl 4,6-O-benzylidene-3-C-(cyanomethyl)-2,3-dideoxy-2-C-(2-iodoethyl)-2-C-methyl-3-C-((E)-1-propenyl)-α-D-allopyranoside (122622-29-1)

Guidance literature:

Multi-step reaction with 16 steps

1: 65 percent / KH / tetrahydrofuran / 3 h / 0 °C

2: 2.) LiAlH₄ / 1.) THF, 15 min, 2.) THF, 0 deg C, 45 min

3: imidazole / tetrahydrofuran / 0.5 h / Ambient temperature

4: 69 percent / SOCl₂, pyridine / tetrahydrofuran / 1 h / 0 °C

5: dimethylformamide / 2 h / 100 °C

6: NaOMe / methanol / Ambient temperature

7: PCC, AcONa, Celite / CH₂Cl₂ / 0.33 h / Ambient temperature

8: tetrahydrofuran / 0.17 h

9: Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature

10: MeLi / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

11: mercuric trifluoroacetate / Ambient temperature

12: xylene / 24 h / Heating

13: hydroxylamine hydrochloride, pyridine

14: trifluoroacetic anhydride, pyridine / CH₂Cl₂ / Ambient temperature

15: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

16: iodine, triphenyl phosphine, imidazole / benzene / 0.08 h / Ambient temperature

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; thionyl chloride; Celite; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; methyllithium; iodine; sodium methylate; sodium acetate; mercury(II) trifluoroacetate; potassium hydride; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic anhydride; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; xylene; benzene;

DOI:10.1021/jo00283a034

upstream raw materials:

(2R,4aR,6S,7R,8S,8aR)-7-(2-Hydroxy-ethyl)-6-methoxy-7-methyl-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

methyl 2-deoxy-2-(2-ethoxy-2-oxoethyl)-4,6-O-(phenylmethylene)-α-D-ribohexopyranosid-3-ulose

methyl 4,6-O-benzylidene-2-deoxy-2-C-((ethoxycarbonyl)methyl)-2-C-methyl-α-D-ribo-hexopyranosid-3-ulose

methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2-deoxy-2-C-methyl-3-C-vinyl-α-D-allopyranoside

Downstream raw materials:

(10R)-methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-glucopyranosido<3,2-c>-10-methylbicyclo<3.3.0>octan-11-one

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