(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

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-dodecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-2,3-diol
CAS No.:1054663-75-0
Molecular Formula:C₃₈H₄₅ClO₉
Molecular Weight:681.223
Hs Code.:

Synonyms:

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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-dodecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-2,3-diol

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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-dodecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-2,3-diol

There total 36 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-dodecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-2,3-diol 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:

: 370886-91-2
(2R,4aR,8S,8aS,2'R,4'S,4'aR,6'R,7'R,8'aR)-8,7'-Bis-benzyloxy-6'-benzyloxymethyl-4'-chloro-2-hydroxy-dodecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-3-one

: 1054663-75-0
(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

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;
DOI:10.1016/S0040-4039(01)01067-X

Reference yield:

: 370887-48-2
(2R,3S,4S)-4-Benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-ol

: 1054663-75-0
(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

Guidance literature:: Multi-step reaction with 13 steps

1: 2,6-lutidine / CH₂Cl₂ / -78 °C

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

3: 100 percent / K₂CO₃ / methanol / 20 °C

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

5: Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / -30 °C

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

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

8: PPh₃; CCl₄ / Heating

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

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

11: HF*pyr / tetrahydrofuran / 20 °C

12: DIBALH / CH₂Cl₂ / -78 °C

With 2,6-dimethylpyridine; triethylsilane; tetrachloromethane; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; potassium carbonate; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; phosphate buffer; dichloromethane; water; 11: Swern oxidation;
DOI:10.1016/S0040-4039(01)01067-X

Reference yield:

: 83122-90-1
1,2-dideoxy-4,6-O-isopropylidine-D-glucopyranose

: 1054663-75-0
(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

Guidance literature:: Multi-step reaction with 17 steps

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

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

3: NaH / dimethylformamide / 0 - 20 °C

4: p-TsOH / methanol / 20 °C

5: 2,6-lutidine / CH₂Cl₂ / -78 °C

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

7: 100 percent / K₂CO₃ / methanol / 20 °C

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

9: Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / -30 °C

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

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

12: PPh₃; CCl₄ / Heating

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

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

15: HF*pyr / tetrahydrofuran / 20 °C

16: DIBALH / CH₂Cl₂ / -78 °C

With 2,6-dimethylpyridine; triethylsilane; tetrachloromethane; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; L-Selectride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; phosphate buffer; dichloromethane; water; N,N-dimethyl-formamide; 15: Swern oxidation;
DOI:10.1016/S0040-4039(01)01067-X