Ethyl (α-Methyl 4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-3-O-(methoxymethyl)-D-manno-D,L-glycero-non-7-eno-1,5-pyranos)uronate

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Chemical Name:Ethyl (α-Methyl 4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-3-O-(methoxymethyl)-D-manno-D,L-glycero-non-7-eno-1,5-pyranos)uronate
CAS No.:137792-65-5
Molecular Formula:C₂₇H₄₃IO₈Si
Molecular Weight:650.624
Hs Code.:

Ethyl (α-Methyl 4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-3-O-(methoxymethyl)-D-manno-D,L-glycero-non-7-eno-1,5-pyranos)uronate

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Chemical Property of Ethyl (α-Methyl 4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-3-O-(methoxymethyl)-D-manno-D,L-glycero-non-7-eno-1,5-pyranos)uronate

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Technology Process of Ethyl (α-Methyl 4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-3-O-(methoxymethyl)-D-manno-D,L-glycero-non-7-eno-1,5-pyranos)uronate

There total 13 articles about Ethyl (α-Methyl 4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-3-O-(methoxymethyl)-D-manno-D,L-glycero-non-7-eno-1,5-pyranos)uronate 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:

: 58871-09-3
6-O-tert-butyldimethylsilyl-D-glucal

: 137792-65-5,137792-90-6
Ethyl (α-Methyl 4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-3-O-(methoxymethyl)-D-manno-D,L-glycero-non-7-eno-1,5-pyranos)uronate

Guidance literature:: Multi-step reaction with 11 steps

1: 9.8 g / pyridine / 0.33 h / -5 °C

2: 1) KH, 2) tetra-n-butylammonium iodide / 1) THF, 0 deg C, 15 min, 2) THF, rt, 6 h

3: 96 percent / diisopropylethylamine / CH₂Cl₂ / 11 h / Ambient temperature

4: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

5: pyridinium chlorochromate, 4-Angstroem molecular sieves / CH₂Cl₂

6: tetrahydrofuran / 1) -78 deg C, 30 min, 2) 0 deg C, 30 min

7: imidazole / dimethylformamide / Ambient temperature

8: 94 percent / N-iodosuccinimide / acetonitrile / 6 h / Ambient temperature

9: OsO₄, N-methylmorpholine oxide / acetone; 2-methyl-propan-2-ol; H₂O

10: Na₂CO₃, Pb(OAc)4 / CH₂Cl₂ / 0.25 h / 0 °C

11: 1) NaH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C

With pyridine; 1H-imidazole; lead(IV) acetate; N-iodo-succinimide; osmium(VIII) oxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; sodium carbonate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo00028a033

Reference yield:

: 100-39-0
benzyl bromide

: 137792-65-5,137792-90-6
Ethyl (α-Methyl 4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-3-O-(methoxymethyl)-D-manno-D,L-glycero-non-7-eno-1,5-pyranos)uronate

Guidance literature:: Multi-step reaction with 10 steps

1: 1) KH, 2) tetra-n-butylammonium iodide / 1) THF, 0 deg C, 15 min, 2) THF, rt, 6 h

2: 96 percent / diisopropylethylamine / CH₂Cl₂ / 11 h / Ambient temperature

3: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

4: pyridinium chlorochromate, 4-Angstroem molecular sieves / CH₂Cl₂

5: tetrahydrofuran / 1) -78 deg C, 30 min, 2) 0 deg C, 30 min

6: imidazole / dimethylformamide / Ambient temperature

7: 94 percent / N-iodosuccinimide / acetonitrile / 6 h / Ambient temperature

8: OsO₄, N-methylmorpholine oxide / acetone; 2-methyl-propan-2-ol; H₂O

9: Na₂CO₃, Pb(OAc)4 / CH₂Cl₂ / 0.25 h / 0 °C

10: 1) NaH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C

With 1H-imidazole; lead(IV) acetate; N-iodo-succinimide; osmium(VIII) oxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; sodium carbonate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo00028a033

Reference yield:

: 137792-86-0
4-O-Benzyl-3-O-(methoxymethyl)-D-glucal

: 137792-65-5,137792-90-6
Ethyl (α-Methyl 4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2,7,8-trideoxy-2-iodo-3-O-(methoxymethyl)-D-manno-D,L-glycero-non-7-eno-1,5-pyranos)uronate

Guidance literature:: Multi-step reaction with 7 steps

1: pyridinium chlorochromate, 4-Angstroem molecular sieves / CH₂Cl₂

2: tetrahydrofuran / 1) -78 deg C, 30 min, 2) 0 deg C, 30 min

3: imidazole / dimethylformamide / Ambient temperature

4: 94 percent / N-iodosuccinimide / acetonitrile / 6 h / Ambient temperature

5: OsO₄, N-methylmorpholine oxide / acetone; 2-methyl-propan-2-ol; H₂O

6: Na₂CO₃, Pb(OAc)4 / CH₂Cl₂ / 0.25 h / 0 °C

7: 1) NaH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C

With 1H-imidazole; lead(IV) acetate; N-iodo-succinimide; osmium(VIII) oxide; 4 A molecular sieve; sodium hydride; sodium carbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo00028a033