(2R,3aR,4R,5R,6R)-hexahydro-4,5-bis(phenylmethoxy)-6-[(phenylmethoxy)methyl]pyrrolo[1,2-b]isoxazole-2-methanol

Base Information

• Chemical Name: (2R,3aR,4R,5R,6R)-hexahydro-4,5-bis(phenylmethoxy)-6-[(phenylmethoxy)methyl]pyrrolo[1,2-b]isoxazole-2-methanol
• CAS No.: 631915-23-6
• Molecular Formula: C₂₉H₃₃NO₅
• Molecular Weight: 475.585
• Mol file: 631915-23-6.mol

Synonyms:(2R,3aR,4R,5R,6R)-hexahydro-4,5-bis(phenylmethoxy)-6-[(phenylmethoxy)methyl]pyrrolo[1,2-b]isoxazole-2-methanol

Chemical Property of (2R,3aR,4R,5R,6R)-hexahydro-4,5-bis(phenylmethoxy)-6-[(phenylmethoxy)methyl]pyrrolo[1,2-b]isoxazole-2-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3aR,4R,5R,6R)-hexahydro-4,5-bis(phenylmethoxy)-6-[(phenylmethoxy)methyl]pyrrolo[1,2-b]isoxazole-2-methanol

There total 5 articles about (2R,3aR,4R,5R,6R)-hexahydro-4,5-bis(phenylmethoxy)-6-[(phenylmethoxy)methyl]pyrrolo[1,2-b]isoxazole-2-methanol 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: 73.0%

allyl alcohol (107-18-6) + (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide (537030-19-6) → (2R,3aR,4R,5R,6R)-hexahydro-4,5-bis(phenylmethoxy)-6-[(phenylmethoxy)methyl]pyrrolo[1,2-b]isoxazole-2-methanol (631915-23-6) + (2S,3aR,4R,5R,6R)-hexahydro-4,5-bis(phenylmethoxy)-6-[(phenylmethoxy)methyl]pyrrolo[1,2-b]isoxazole-2-methanol

Guidance literature:

In toluene; for 3h; Heating;

DOI:10.1002/hlca.200390248

Reference yield:

2,3,5-tri-O-benzyl-D-arabinofuranose (160549-10-0) → (2R,3aR,4R,5R,6R)-hexahydro-4,5-bis(phenylmethoxy)-6-[(phenylmethoxy)methyl]pyrrolo[1,2-b]isoxazole-2-methanol (631915-23-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / NH₂OH*HCl; NaOMe / methanol

2: 92 percent / pyridine / 25 °C

3: 54 percent / Ph₃P; 1H-imidazole; I₂ / toluene / 2 h / Heating

4: 92 percent / Bu₄NF / toluene / 0.5 h / Heating

5: 73 percent / toluene / 3 h / Heating

With pyridine; 1H-imidazole; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; iodine; sodium methylate; triphenylphosphine; In methanol; toluene;

DOI:10.1002/hlca.200390248

Reference yield:

(E/Z)-2,3,5-tri-O-benzyl-D-arabinose-oxime (620946-66-9) → (2R,3aR,4R,5R,6R)-hexahydro-4,5-bis(phenylmethoxy)-6-[(phenylmethoxy)methyl]pyrrolo[1,2-b]isoxazole-2-methanol (631915-23-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / pyridine / 25 °C

2: 54 percent / Ph₃P; 1H-imidazole; I₂ / toluene / 2 h / Heating

3: 92 percent / Bu₄NF / toluene / 0.5 h / Heating

4: 73 percent / toluene / 3 h / Heating

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; iodine; triphenylphosphine; In toluene;

DOI:10.1002/hlca.200390248

upstream raw materials:

allyl alcohol

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide

2,3,5-tri-O-benzyl-D-arabinofuranose

(E/Z)-2,3,5-tri-O-benzyl-D-arabinose-oxime

Downstream raw materials:

(2S,3aR,4R,5R,6R)-hexahydro-4,5-bis(phenylmethoxy)-6-[(phenylmethoxy)methyl]pyrrolo[1,2-b]isoxazole-2-methanol methanesulfonate

(1S,2R,3R,6R,7aR)-hexahydro-1,2-bis(phenylmethoxy)-3-[(phenylmethoxy)methyl]-1H-pyrrolizine-6-ol