(2S,3S,4aR,8S,8aS,2'R,4'S,4'aR,6'R,7'R,8'aR)-8,7'-Bis-benzyloxy-6'-benzyloxymethyl-4'-chloro-hexadecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-3-ol

Base Information

• Chemical Name: (2S,3S,4aR,8S,8aS,2'R,4'S,4'aR,6'R,7'R,8'aR)-8,7'-Bis-benzyloxy-6'-benzyloxymethyl-4'-chloro-hexadecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-3-ol
• CAS No.: 370886-93-4
• Molecular Formula: C₃₈H₄₅ClO₈
• Molecular Weight: 665.223
• Mol file: 370886-93-4.mol

Synonyms:

Chemical Property of (2S,3S,4aR,8S,8aS,2'R,4'S,4'aR,6'R,7'R,8'aR)-8,7'-Bis-benzyloxy-6'-benzyloxymethyl-4'-chloro-hexadecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4aR,8S,8aS,2'R,4'S,4'aR,6'R,7'R,8'aR)-8,7'-Bis-benzyloxy-6'-benzyloxymethyl-4'-chloro-hexadecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-3-ol

There total 25 articles about (2S,3S,4aR,8S,8aS,2'R,4'S,4'aR,6'R,7'R,8'aR)-8,7'-Bis-benzyloxy-6'-benzyloxymethyl-4'-chloro-hexadecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-3-ol 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:

(2R,4aR,6S,7R)-2-Phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol → (2S,3S,4aR,8S,8aS,2'R,4'S,4'aR,6'R,7'R,8'aR)-8,7'-Bis-benzyloxy-6'-benzyloxymethyl-4'-chloro-hexadecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-3-ol (370886-93-4)

Guidance literature:

Multi-step reaction with 25 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2.1: CSA / methanol; CH₂Cl₂ / 20 °C

3.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

4.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

5.1: L-selectride / tetrahydrofuran / -78 °C

6.1: CSA / methanol; CH₂Cl₂ / 20 °C

7.1: NaH / dimethylformamide / 0 - 20 °C

8.1: OsO₄; NMO / acetone; H₂O / 20 °C

9.1: NaIO₄ / tetrahydrofuran; H₂O / 20 °C

10.1: MgBr₂*OEt₂ / CH₂Cl₂ / -78 - 20 °C

11.1: t-BuOK; n-Bu₄NI / tetrahydrofuran / 0 - 20 °C

12.1: n-Bu₄NF / tetrahydrofuran / 20 °C

13.1: OsO₄; NMO / tetrahydrofuran; H₂O / 20 °C

14.1: NaIO₄ / tetrahydrofuran; H₂O / 20 °C

15.1: 100 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

16.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

17.1: Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / -30 °C

18.1: H₂ / Lindlar catalyst / methanol / 20 °C

19.1: DDQ / CH₂Cl₂; aq. phosphate buffer / 20 °C / pH 7.0

20.1: PPh₃; CCl₄ / Heating

21.1: OsO₄; NMO / tetrahydrofuran; H₂O / 20 °C

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

23.1: HF*pyr / tetrahydrofuran / 20 °C

24.1: DIBALH / CH₂Cl₂ / -78 °C

25.1: p-TsOH / 60 °C

25.2: Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; triethylsilane; tetrachloromethane; dmap; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; L-Selectride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; phosphate buffer; dichloromethane; water; N,N-dimethyl-formamide; acetone; 22.1: Swern oxidation;

DOI:10.1016/S0040-4039(01)01067-X

Reference yield:

(2R,3R,5R,6S)-2-Hydroxymethyl-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol (370886-76-3) → (2S,3S,4aR,8S,8aS,2'R,4'S,4'aR,6'R,7'R,8'aR)-8,7'-Bis-benzyloxy-6'-benzyloxymethyl-4'-chloro-hexadecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-3-ol (370886-93-4)

Guidance literature:

Multi-step reaction with 19 steps

1.1: NaH / dimethylformamide / 0 - 20 °C

2.1: OsO₄; NMO / acetone; H₂O / 20 °C

3.1: NaIO₄ / tetrahydrofuran; H₂O / 20 °C

4.1: MgBr₂*OEt₂ / CH₂Cl₂ / -78 - 20 °C

5.1: t-BuOK; n-Bu₄NI / tetrahydrofuran / 0 - 20 °C

6.1: n-Bu₄NF / tetrahydrofuran / 20 °C

7.1: OsO₄; NMO / tetrahydrofuran; H₂O / 20 °C

8.1: NaIO₄ / tetrahydrofuran; H₂O / 20 °C

9.1: 100 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

10.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

11.1: Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / -30 °C

12.1: H₂ / Lindlar catalyst / methanol / 20 °C

13.1: DDQ / CH₂Cl₂; aq. phosphate buffer / 20 °C / pH 7.0

14.1: PPh₃; CCl₄ / Heating

15.1: OsO₄; NMO / tetrahydrofuran; H₂O / 20 °C

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

17.1: HF*pyr / tetrahydrofuran / 20 °C

18.1: DIBALH / CH₂Cl₂ / -78 °C

19.1: p-TsOH / 60 °C

19.2: Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 0 °C

With triethylsilane; tetrachloromethane; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; phosphate buffer; dichloromethane; water; N,N-dimethyl-formamide; acetone; 16.1: Swern oxidation;

DOI:10.1016/S0040-4039(01)01067-X

Reference yield:

(2R,3S,5R,6S)-2-Hydroxymethyl-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol (370886-82-1) → (2S,3S,4aR,8S,8aS,2'R,4'S,4'aR,6'R,7'R,8'aR)-8,7'-Bis-benzyloxy-6'-benzyloxymethyl-4'-chloro-hexadecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-3-ol (370886-93-4)

Guidance literature:

Multi-step reaction with 23 steps

1.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

3.1: L-selectride / tetrahydrofuran / -78 °C

4.1: CSA / methanol; CH₂Cl₂ / 20 °C

5.1: NaH / dimethylformamide / 0 - 20 °C

6.1: OsO₄; NMO / acetone; H₂O / 20 °C

7.1: NaIO₄ / tetrahydrofuran; H₂O / 20 °C

8.1: MgBr₂*OEt₂ / CH₂Cl₂ / -78 - 20 °C

9.1: t-BuOK; n-Bu₄NI / tetrahydrofuran / 0 - 20 °C

10.1: n-Bu₄NF / tetrahydrofuran / 20 °C

11.1: OsO₄; NMO / tetrahydrofuran; H₂O / 20 °C

12.1: NaIO₄ / tetrahydrofuran; H₂O / 20 °C

13.1: 100 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

14.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

15.1: Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / -30 °C

16.1: H₂ / Lindlar catalyst / methanol / 20 °C

17.1: DDQ / CH₂Cl₂; aq. phosphate buffer / 20 °C / pH 7.0

18.1: PPh₃; CCl₄ / Heating

19.1: OsO₄; NMO / tetrahydrofuran; H₂O / 20 °C

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

21.1: HF*pyr / tetrahydrofuran / 20 °C

22.1: DIBALH / CH₂Cl₂ / -78 °C

23.1: p-TsOH / 60 °C

23.2: Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 0 °C

With triethylsilane; tetrachloromethane; dmap; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; L-Selectride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; phosphate buffer; dichloromethane; water; N,N-dimethyl-formamide; acetone; 20.1: Swern oxidation;

DOI:10.1016/S0040-4039(01)01067-X

upstream raw materials:

methanol

(2S,3S,4aR,8S,8aS,2'R,4'S,4'aR,6'R,7'R,8'aR)-8,7'-Bis-benzyloxy-6'-benzyloxymethyl-4'-chloro-dodecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-2,3-diol

(2R,3S,5R,6S)-2-Hydroxymethyl-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol

(2R,3R,5R,6S)-2-Hydroxymethyl-5-triisopropylsilanyloxy-6-vinyl-tetrahydro-pyran-3-ol