(2R,3aR,6R,7S,7aS)-6-Acetoxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-phenoxythiocarbonyloxy-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,3aR,6R,7S,7aS)-6-Acetoxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-phenoxythiocarbonyloxy-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester
CAS No.:905578-60-1
Molecular Formula:C₂₇H₃₅NO₁₂S
Molecular Weight:597.64
Hs Code.:

(2R,3aR,6R,7S,7aS)-6-Acetoxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-phenoxythiocarbonyloxy-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Synonyms:(2R,3aR,6R,7S,7aS)-6-Acetoxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-phenoxythiocarbonyloxy-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Suppliers and Price of (2R,3aR,6R,7S,7aS)-6-Acetoxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-phenoxythiocarbonyloxy-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl 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 (2R,3aR,6R,7S,7aS)-6-Acetoxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-phenoxythiocarbonyloxy-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (2R,3aR,6R,7S,7aS)-6-Acetoxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-phenoxythiocarbonyloxy-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

There total 22 articles about (2R,3aR,6R,7S,7aS)-6-Acetoxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-phenoxythiocarbonyloxy-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl 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: 70.0%

: 905578-55-4
(2R,3aR,6R,7S,7aR)-6-Acetoxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-hydroxy-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

: 1005-56-7
phenylcarbonochloridothioate

: 905578-60-1
(2R,3aR,6R,7S,7aS)-6-Acetoxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-phenoxythiocarbonyloxy-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Guidance literature:: With dmap; In toluene; for 3h; Heating;
DOI:10.1021/jo0605593

Reference yield:

: 905578-50-9
((3aS,5aR,8aS,8bS)-7-Benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-ylmethoxy)-tert-butyl-dimethyl-silane

: 905578-60-1
(2R,3aR,6R,7S,7aS)-6-Acetoxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-phenoxythiocarbonyloxy-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 75 percent / hydrogen / Pd/C / hexane / 2 h / 20 °C

2: SO₃*pyridine; DMSO; triethylamine / CH₂Cl₂ / 1.5 h / 20 °C

3: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

4: 10.6 g / methanol; benzene; diethyl ether / 20 °C

5: 85 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

6: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.75 h / -78 - 20 °C

7: 5.65 g / N,N,N',N'-tetramethylguanidine / CH₂Cl₂ / 1 h / 20 °C

8: 85 percent / hydrogen / [Rh(COD){(S,S)-EtDuPHOS}]OTf / tetrahydrofuran / 96 h / 20 °C / 6000.48 Torr

9: 100 percent / hydrogen / Pd(OH)2/C / hexane; methanol / 2 h / 20 °C

10: 80 percent / DDQ / acetonitrile; H₂O / 12 h / 55 °C

11: 265 mg / thionyl chloride; triethylamine / CH₂Cl₂ / 0.5 h / -20 °C

12: 245 mg / NaIO₄ / RuCl₃ / acetonitrile; CCl₄; H₂O / 1 h / 20 °C

13: dimethylformamide / 6 h / 65 °C

14: 68.0 mg / H₂SO₄ / tetrahydrofuran / 1 h / 20 °C

15: 70 percent / DMAP / toluene / 3 h / Heating

With dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; thionyl chloride; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; N,N,N',N'-tetramethylguanidine; ruthenium trichloride; palladium dihydroxide; palladium on activated charcoal; [(1,2,5,6-r)-1,5-cyclooctadiene][(2S,2'S,5 S,5'S)-1,1'-(1,2-phenylene)bis[2,5-diethylphospholane-κP]]-rhodium(1+) trifluoromethanesulfonate; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene; 6: Swern oxidation / 7: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jo0605593

Reference yield:

: (3aS,5aR,7S,8aS,8bS)-7-Formyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

: 905578-60-1
(2R,3aR,6R,7S,7aS)-6-Acetoxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-phenoxythiocarbonyloxy-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 5.65 g / N,N,N',N'-tetramethylguanidine / CH₂Cl₂ / 1 h / 20 °C

2: 85 percent / hydrogen / [Rh(COD){(S,S)-EtDuPHOS}]OTf / tetrahydrofuran / 96 h / 20 °C / 6000.48 Torr

3: 100 percent / hydrogen / Pd(OH)2/C / hexane; methanol / 2 h / 20 °C

4: 80 percent / DDQ / acetonitrile; H₂O / 12 h / 55 °C

5: 265 mg / thionyl chloride; triethylamine / CH₂Cl₂ / 0.5 h / -20 °C

6: 245 mg / NaIO₄ / RuCl₃ / acetonitrile; CCl₄; H₂O / 1 h / 20 °C

7: dimethylformamide / 6 h / 65 °C

8: 68.0 mg / H₂SO₄ / tetrahydrofuran / 1 h / 20 °C

9: 70 percent / DMAP / toluene / 3 h / Heating

With dmap; sodium periodate; thionyl chloride; sulfuric acid; hydrogen; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; N,N,N',N'-tetramethylguanidine; ruthenium trichloride; palladium dihydroxide; [(1,2,5,6-r)-1,5-cyclooctadiene][(2S,2'S,5 S,5'S)-1,1'-(1,2-phenylene)bis[2,5-diethylphospholane-κP]]-rhodium(1+) trifluoromethanesulfonate; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jo0605593