(2R,4aR,8S,8aR)-8-Chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

• Chemical Name: (2R,4aR,8S,8aR)-8-Chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS No.: 909544-94-1
• Molecular Formula: C₁₃H₁₅ClO₃
• Molecular Weight: 254.713
• Mol file: 909544-94-1.mol

Synonyms:(2R,4aR,8S,8aR)-8-Chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property of (2R,4aR,8S,8aR)-8-Chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,8S,8aR)-8-Chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 1 articles about (2R,4aR,8S,8aR)-8-Chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 89.0%

1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside (135214-83-4) → (2R,4aR,8S,8aR)-8-Chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (909544-94-1)

Guidance literature:

With tetrachloromethane; potassium carbonate; triphenylphosphine; at 80 ℃;

DOI:10.1016/j.tetlet.2006.06.032

Reference yield:

(2R,4aR,8S,8aR)-8-Chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (909544-94-1) → (2S,3R,4aR,8S,8aR,2'R,4'aS,6'R,7'S,8'S,8'aS)-7',8'-Bis-benzyloxy-6'-benzyloxymethyl-8-chloro-hexadecahydro-[2,2']bi[pyrano[3,2-b]pyranyl]-3-ol (909544-92-9)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 100 percent / camphorsulfonic acid / methanol

2.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

3.1: camphorsulfonic acid / methanol / 0 °C

4.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

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

6.1: 100 percent / K₂CO₃ / methanol

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

7.2: 81 percent / tetrahydrofuran; hexamethylphosphoric acid triamide

8.1: 100 percent / (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

9.1: 79 percent / HF / acetonitrile / 0 °C

10.1: 94 percent / Et₃SiH; BF₃*OEt₂ / acetonitrile / 0 °C

11.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

12.1: 100 percent / H₂; quinoline / Lindlar catalyst / ethyl acetate

13.1: 95 percent / OSO₄; H₂O; NMO / tetrahydrofuran

14.1: trifluoroacetic anhydride; DMSO; triethylamine / CH₂Cl₂ / -60 °C

15.1: HF / acetonitrile / 0 °C

16.1: 22 percent / DIBALH / CH₂Cl₂ / -78 °C

17.1: 75 percent / p-toluenesulfonic acid / 70 °C

18.1: 22 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; quinoline; triethylsilane; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen fluoride; water; hydrogen; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; acetonitrile; 8.1: Swern oxidation;

DOI:10.1016/j.tetlet.2006.06.032

Reference yield:

(2R,4aR,8S,8aR)-8-Chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (909544-94-1) → 1-((2R,4aS,6R,7S,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-3-[(2R,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-chloro-tetrahydro-pyran-2-yl]-propane-1,2-diol (909544-87-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 100 percent / camphorsulfonic acid / methanol

2.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

3.1: camphorsulfonic acid / methanol / 0 °C

4.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

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

6.1: 100 percent / K₂CO₃ / methanol

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

7.2: 81 percent / tetrahydrofuran; hexamethylphosphoric acid triamide

8.1: 100 percent / (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

9.1: 79 percent / HF / acetonitrile / 0 °C

10.1: 94 percent / Et₃SiH; BF₃*OEt₂ / acetonitrile / 0 °C

11.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

12.1: 100 percent / H₂; quinoline / Lindlar catalyst / ethyl acetate

13.1: 95 percent / OSO₄; H₂O; NMO / tetrahydrofuran

With 2,6-dimethylpyridine; quinoline; triethylsilane; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen fluoride; water; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; acetonitrile; 8.1: Swern oxidation;

DOI:10.1016/j.tetlet.2006.06.032

upstream raw materials:

1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside

Downstream raw materials:

(2R,3R,4S)-2-[3-((2R,4aS,6R,7S,8S,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran-2-yl)-prop-2-ynyl]-4-chloro-tetrahydro-pyran-3-ol

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

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

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