((1R,3S,4S,5S,6R,7S,8R)-7-Benzyloxy-6-hydroxy-3-methoxy-8-methoxymethoxy-2-oxa-bicyclo[2.2.2]oct-5-yl)-acetic acid ethyl ester

Base Information

Chemical Name:((1R,3S,4S,5S,6R,7S,8R)-7-Benzyloxy-6-hydroxy-3-methoxy-8-methoxymethoxy-2-oxa-bicyclo[2.2.2]oct-5-yl)-acetic acid ethyl ester
CAS No.:137894-31-6
Molecular Formula:C₂₁H₃₀O₈
Molecular Weight:410.464
Hs Code.:

Synonyms:

Suppliers and Price of ((1R,3S,4S,5S,6R,7S,8R)-7-Benzyloxy-6-hydroxy-3-methoxy-8-methoxymethoxy-2-oxa-bicyclo[2.2.2]oct-5-yl)-acetic acid ethyl ester

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of ((1R,3S,4S,5S,6R,7S,8R)-7-Benzyloxy-6-hydroxy-3-methoxy-8-methoxymethoxy-2-oxa-bicyclo[2.2.2]oct-5-yl)-acetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of ((1R,3S,4S,5S,6R,7S,8R)-7-Benzyloxy-6-hydroxy-3-methoxy-8-methoxymethoxy-2-oxa-bicyclo[2.2.2]oct-5-yl)-acetic acid ethyl ester

There total 15 articles about ((1R,3S,4S,5S,6R,7S,8R)-7-Benzyloxy-6-hydroxy-3-methoxy-8-methoxymethoxy-2-oxa-bicyclo[2.2.2]oct-5-yl)-acetic acid ethyl 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:

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

: 137894-31-6
((1R,3S,4S,5S,6R,7S,8R)-7-Benzyloxy-6-hydroxy-3-methoxy-8-methoxymethoxy-2-oxa-bicyclo[2.2.2]oct-5-yl)-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 13 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

12: 31 mg / n-Bu₃SnH, AIBN / toluene / Heating

13: n-Bu₄NF / tetrahydrofuran / Ambient temperature

With pyridine; 1H-imidazole; lead(IV) acetate; N-iodo-succinimide; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; 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; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo00028a033

Reference yield:

: 100-39-0
benzyl bromide

: 137894-31-6
((1R,3S,4S,5S,6R,7S,8R)-7-Benzyloxy-6-hydroxy-3-methoxy-8-methoxymethoxy-2-oxa-bicyclo[2.2.2]oct-5-yl)-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 12 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

11: 31 mg / n-Bu₃SnH, AIBN / toluene / Heating

12: n-Bu₄NF / tetrahydrofuran / Ambient temperature

With 1H-imidazole; lead(IV) acetate; N-iodo-succinimide; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; 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; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo00028a033

Reference yield:

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

: 137894-31-6
((1R,3S,4S,5S,6R,7S,8R)-7-Benzyloxy-6-hydroxy-3-methoxy-8-methoxymethoxy-2-oxa-bicyclo[2.2.2]oct-5-yl)-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 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

8: 31 mg / n-Bu₃SnH, AIBN / toluene / Heating

9: n-Bu₄NF / tetrahydrofuran / Ambient temperature

With 1H-imidazole; lead(IV) acetate; N-iodo-succinimide; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; sodium carbonate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo00028a033