(3aS,4R,5aR,7R,8aS,8bR)-4-Acetoxymethyl-7-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

Base Information

• Chemical Name: (3aS,4R,5aR,7R,8aS,8bR)-4-Acetoxymethyl-7-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester
• CAS No.: 916044-56-9
• Molecular Formula: C₂₇H₃₅NO₁₂
• Molecular Weight: 565.574
• Mol file: 916044-56-9.mol

Synonyms:(3aS,4R,5aR,7R,8aS,8bR)-4-Acetoxymethyl-7-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

Chemical Property of (3aS,4R,5aR,7R,8aS,8bR)-4-Acetoxymethyl-7-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4R,5aR,7R,8aS,8bR)-4-Acetoxymethyl-7-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

There total 14 articles about (3aS,4R,5aR,7R,8aS,8bR)-4-Acetoxymethyl-7-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-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: 74.0%

(3aS,4R,5aR,7S,8aS,8bR)-4-Acetoxymethyl-7-((Z)-2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester → (3aS,4R,5aR,7R,8aS,8bR)-4-Acetoxymethyl-7-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester (916044-56-9)

Guidance literature:

With [(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; hydrogen; In tetrahydrofuran; at 20 ℃; under 6000.48 Torr;

DOI:10.1016/j.bmcl.2006.08.082

Reference yield:

Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-(2-benzyloxymethyl-allyl)-3,6-dihydro-2H-pyran-3-yl ester (916044-44-5) → (3aS,4R,5aR,7R,8aS,8bR)-4-Acetoxymethyl-7-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester (916044-56-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 83 percent / (DHQD)2AQN; aq. K₂CO₃; K₂[Fe(CN)6] / OsO₄; MeSO₂NH₂ / 2-methyl-propan-2-ol / 0 °C

2: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

3: 98 percent / Pd₂(dba)3; neocuproine / toluene / 60 °C

4: 92 percent / OsO₄; NMO / acetone; H₂O / 20 °C

5: 92 percent / CSA / CH₂Cl₂ / 20 °C

6: 85 percent / H₂ / Pd/C / hexane / 20 °C

7: SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / 20 °C

8: NaClO₂; aq. NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 20 °C

9: benzene; methanol / 20 °C

10: 100 percent / TBAF / tetrahydrofuran / 20 °C

11: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

12: tetramethylguanidine / CH₂Cl₂ / 0 °C

13: 74 percent / H₂; [Rh(I)(-COD)(S,S)-Et-DuPHOS]⁽¹⁺⁾*OTf^(1-) / tetrahydrofuran / 20 °C / 6000.48 Torr

With dmap; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; [(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; N-methyl-2-indolinone; 2-methyl-but-2-ene; oxalyl dichloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; hydroquinidine anthraquinone-1,4-diyl diether; 2.9-dimethyl-1,10-phenanthroline; pyridine-SO₃ complex; 1,1,3,3-tetramethylguanidine; K₂[Fe(CN)6]; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; osmium(VIII) oxide; methanesulfonamide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene; 11: Swern oxidation / 12: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.bmcl.2006.08.082

Reference yield:

Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-(3-benzyloxy-2-hydroxy-2-hydroxymethyl-propyl)-3,6-dihydro-2H-pyran-3-yl ester → (3aS,4R,5aR,7R,8aS,8bR)-4-Acetoxymethyl-7-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester (916044-56-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2: 98 percent / Pd₂(dba)3; neocuproine / toluene / 60 °C

3: 92 percent / OsO₄; NMO / acetone; H₂O / 20 °C

4: 92 percent / CSA / CH₂Cl₂ / 20 °C

5: 85 percent / H₂ / Pd/C / hexane / 20 °C

6: SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / 20 °C

7: NaClO₂; aq. NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 20 °C

8: benzene; methanol / 20 °C

9: 100 percent / TBAF / tetrahydrofuran / 20 °C

10: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

11: tetramethylguanidine / CH₂Cl₂ / 0 °C

12: 74 percent / H₂; [Rh(I)(-COD)(S,S)-Et-DuPHOS]⁽¹⁺⁾*OTf^(1-) / tetrahydrofuran / 20 °C / 6000.48 Torr

With dmap; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; [(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; N-methyl-2-indolinone; 2-methyl-but-2-ene; oxalyl dichloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; 2.9-dimethyl-1,10-phenanthroline; pyridine-SO₃ complex; 1,1,3,3-tetramethylguanidine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene; 10: Swern oxidation / 11: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.bmcl.2006.08.082

upstream raw materials:

Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-(2-benzyloxymethyl-allyl)-3,6-dihydro-2H-pyran-3-yl ester

(3aS,4R,5aR,7S,8aS,8bR)-4-Acetoxymethyl-7-hydroxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

Acetic acid (3aS,4R,5aR,7R,8aS,8bR)-7-(tert-butyl-dimethyl-silanyloxymethyl)-7-hydroxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-4-ylmethyl ester

(3aS,4R,5aR,7S,8aS,8bR)-4-Acetoxymethyl-7-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester