1-((2R,4S,4aR,6R,7R,8aR)-7-Benzyloxy-6-benzyloxymethyl-4-chloro-octahydro-pyrano[3,2-b]pyran-2-yl)-3-[(2R,3S,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propane-1,2-diol

Base Information

• Chemical Name: 1-((2R,4S,4aR,6R,7R,8aR)-7-Benzyloxy-6-benzyloxymethyl-4-chloro-octahydro-pyrano[3,2-b]pyran-2-yl)-3-[(2R,3S,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propane-1,2-diol
• CAS No.: 675834-58-9
• Molecular Formula: C₄₄H₆₁ClO₉Si
• Molecular Weight: 797.501
• Mol file: 675834-58-9.mol

Synonyms:

Chemical Property of 1-((2R,4S,4aR,6R,7R,8aR)-7-Benzyloxy-6-benzyloxymethyl-4-chloro-octahydro-pyrano[3,2-b]pyran-2-yl)-3-[(2R,3S,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((2R,4S,4aR,6R,7R,8aR)-7-Benzyloxy-6-benzyloxymethyl-4-chloro-octahydro-pyrano[3,2-b]pyran-2-yl)-3-[(2R,3S,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propane-1,2-diol

There total 33 articles about 1-((2R,4S,4aR,6R,7R,8aR)-7-Benzyloxy-6-benzyloxymethyl-4-chloro-octahydro-pyrano[3,2-b]pyran-2-yl)-3-[(2R,3S,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propane-1,2-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:

{(2R,3R,4S)-4-Benzyloxy-2-[(Z)-3-((2R,4S,4aR,6R,7R,8aR)-7-benzyloxy-6-benzyloxymethyl-4-chloro-octahydro-pyrano[3,2-b]pyran-2-yl)-allyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane (370886-89-8) → 1-((2R,4S,4aR,6R,7R,8aR)-7-Benzyloxy-6-benzyloxymethyl-4-chloro-octahydro-pyrano[3,2-b]pyran-2-yl)-3-[(2R,3S,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propane-1,2-diol (675834-58-9)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; In tetrahydrofuran; water; at 20 ℃;

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

Reference yield:

(2R,3S,4S)-4-Benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-ol (370887-48-2) → 1-((2R,4S,4aR,6R,7R,8aR)-7-Benzyloxy-6-benzyloxymethyl-4-chloro-octahydro-pyrano[3,2-b]pyran-2-yl)-3-[(2R,3S,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propane-1,2-diol (675834-58-9)

Guidance literature:

Multi-step reaction with 10 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

With 2,6-dimethylpyridine; triethylsilane; tetrachloromethane; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; 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;

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

Reference yield:

(3S,4R)-dihydroxy-(2R)-(hydroxymethyl)tetrahydropyran (3971-47-9,7103-29-9,13035-11-5,26242-03-5) → 1-((2R,4S,4aR,6R,7R,8aR)-7-Benzyloxy-6-benzyloxymethyl-4-chloro-octahydro-pyrano[3,2-b]pyran-2-yl)-3-[(2R,3S,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propane-1,2-diol (675834-58-9)

Guidance literature:

Multi-step reaction with 15 steps

1: 100 percent / PPTS / dimethylformamide / 20 °C

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

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

4: NaH / dimethylformamide / 0 - 20 °C

5: p-TsOH / methanol / 20 °C

6: 2,6-lutidine / CH₂Cl₂ / -78 °C

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

8: 100 percent / K₂CO₃ / methanol / 20 °C

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

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

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

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

13: PPh₃; CCl₄ / Heating

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

With 2,6-dimethylpyridine; triethylsilane; tetrachloromethane; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; pyridinium p-toluenesulfonate; L-Selectride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 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;

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

upstream raw materials:

{(2R,3R,4S)-4-Benzyloxy-2-[(Z)-3-((2R,4S,4aR,6R,7R,8aR)-7-benzyloxy-6-benzyloxymethyl-4-chloro-octahydro-pyrano[3,2-b]pyran-2-yl)-allyl]-tetrahydro-pyran-3-yloxy}-tert-butyl-dimethyl-silane

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

1,2-dideoxy-4,6-O-isopropylidine-D-glucopyranose

(3S,4R)-dihydroxy-(2R)-(hydroxymethyl)tetrahydropyran

Downstream raw materials:

1-((2R,4S,4aR,6R,7R,8aR)-7-Benzyloxy-6-benzyloxymethyl-4-chloro-octahydro-pyrano[3,2-b]pyran-2-yl)-3-[(2R,3S,4S)-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-propane-1,2-dione

(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

(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

(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