Acetic acid (1S,2R)-2-acetoxy-1-((2R,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propyl ester

Base Information

Chemical Name:Acetic acid (1S,2R)-2-acetoxy-1-((2R,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propyl ester
CAS No.:181266-76-2
Molecular Formula:C₄₄H₅₄O₁₁
Molecular Weight:758.906
Hs Code.:

Acetic acid (1S,2R)-2-acetoxy-1-((2R,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propyl ester

Synonyms:Acetic acid (1S,2R)-2-acetoxy-1-((2R,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propyl ester

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Chemical Property of Acetic acid (1S,2R)-2-acetoxy-1-((2R,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propyl ester

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Technology Process of Acetic acid (1S,2R)-2-acetoxy-1-((2R,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propyl ester

There total 40 articles about Acetic acid (1S,2R)-2-acetoxy-1-((2R,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propyl 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: 92.0%

: 108-24-7
acetic anhydride

: 181488-55-1
(1S,2R)-1-((2S,3S,4aS,8aR)-3-Benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propane-1,2-diol

: 181266-76-2
Acetic acid (1S,2R)-2-acetoxy-1-((2R,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propyl ester

Guidance literature:: With pyridine; at 65 ℃; for 2h;
DOI:10.1021/ja961230+

Reference yield:

: 40653-15-4
methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside

: 181266-76-2
Acetic acid (1S,2R)-2-acetoxy-1-((2R,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propyl ester

Guidance literature:: Multi-step reaction with 18 steps

1: 71 percent / benzene / 2 h / 23 °C

2: 100 percent / H₂ / Lindlar catalyst / ethyl acetate / 16 h / 23 °C

3: 96 percent / DIBAL / CH₂Cl₂ / 0.25 h / 0 °C

4: 99 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

5: 100 percent / H₂ / Pd(OH)2/C / methanol / 12 h / 23 °C

6: 92 percent / NaH / dimethylformamide / 4 h / 23 °C

7: 88 percent / HBF₄ / dimethylformamide / 12 h / 23 °C

8: DIBAL / CH₂Cl₂ / 1 h / 0 °C

9: 93 percent / NaH, n-Bu₄NI / tetrahydrofuran; dimethylformamide / 2.5 h / 23 °C

10: 80 percent / CAN / acetonitrile; H₂O / 0.67 h / 23 °C

11: 1.) NaH, imidazole, CS₂, MeI, 2.) Bu₃SnH, AIBN / 1.) THF, 2.) toluene, 110 deg C, 0.5 h

12: 85 percent / aq. CF₃COOH / tetrahydrofuran / 26 h / 65 °C

13: 76 percent / (COCl)2, DMSO / CH₂Cl₂ / -78 °C

14: 1.) n-BuLi / 1.) THF, from -78 deg C to 0 deg C, 70 min, 2.) THF, from -78 deg C to 23 deg C

15: 83 percent / Et₃SiH, BF₃*Et₂O / CH₂Cl₂; acetonitrile / 0.5 h / -25 °C

16: 1.) Ph₃SnH, Et₃B, 2.) NIS, 3.) n-BuLi

17: OsO₄, NMO / 2-methyl-propan-2-ol; acetone; H₂O / 96 h / 23 °C

18: 92 percent / pyridine / 2 h / 65 °C

With pyridine; 1H-imidazole; triethylsilane; carbon disulfide; N-iodo-succinimide; osmium(VIII) oxide; tetrafluoroboric acid; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); triethyl borane; boron trifluoride diethyl etherate; triphenylstannane; hydrogen; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; methyl iodide; palladium dihydroxide; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; benzene;
DOI:10.1021/ja961230+

Reference yield:

: 181265-87-2
3-((2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propan-1-ol

: 181266-76-2
Acetic acid (1S,2R)-2-acetoxy-1-((2R,3S,4aS,8aR)-3-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-3-((2R,3R,4S,4aS,8aS)-3,4-bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 99 percent / Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

2: 100 percent / H₂ / Pd(OH)2/C / methanol / 12 h / 23 °C

3: 92 percent / NaH / dimethylformamide / 4 h / 23 °C

4: 88 percent / HBF₄ / dimethylformamide / 12 h / 23 °C

5: DIBAL / CH₂Cl₂ / 1 h / 0 °C

6: 93 percent / NaH, n-Bu₄NI / tetrahydrofuran; dimethylformamide / 2.5 h / 23 °C

7: 80 percent / CAN / acetonitrile; H₂O / 0.67 h / 23 °C

8: 1.) NaH, imidazole, CS₂, MeI, 2.) Bu₃SnH, AIBN / 1.) THF, 2.) toluene, 110 deg C, 0.5 h

9: 85 percent / aq. CF₃COOH / tetrahydrofuran / 26 h / 65 °C

10: 76 percent / (COCl)2, DMSO / CH₂Cl₂ / -78 °C

11: 1.) n-BuLi / 1.) THF, from -78 deg C to 0 deg C, 70 min, 2.) THF, from -78 deg C to 23 deg C

12: 83 percent / Et₃SiH, BF₃*Et₂O / CH₂Cl₂; acetonitrile / 0.5 h / -25 °C

13: 1.) Ph₃SnH, Et₃B, 2.) NIS, 3.) n-BuLi

14: OsO₄, NMO / 2-methyl-propan-2-ol; acetone; H₂O / 96 h / 23 °C

15: 92 percent / pyridine / 2 h / 65 °C

With pyridine; 1H-imidazole; triethylsilane; carbon disulfide; N-iodo-succinimide; osmium(VIII) oxide; tetrafluoroboric acid; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); triethyl borane; boron trifluoride diethyl etherate; triphenylstannane; hydrogen; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; methyl iodide; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja961230+