[(R)-((3aR,4R,4aR,7aR,8R,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl)-hydroxy-methyl]-phosphonic acid dibenzyl ester

Base Information

• Chemical Name: [(R)-((3aR,4R,4aR,7aR,8R,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl)-hydroxy-methyl]-phosphonic acid dibenzyl ester
• CAS No.: 444902-87-8
• Molecular Formula: C₃₄H₄₁O₉P
• Molecular Weight: 624.668
• Mol file: 444902-87-8.mol

Synonyms:

Chemical Property of [(R)-((3aR,4R,4aR,7aR,8R,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl)-hydroxy-methyl]-phosphonic acid dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(R)-((3aR,4R,4aR,7aR,8R,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl)-hydroxy-methyl]-phosphonic acid dibenzyl ester

There total 2 articles about [(R)-((3aR,4R,4aR,7aR,8R,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl)-hydroxy-methyl]-phosphonic acid dibenzyl ester 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:

Dibenzyl phosphite (17176-77-1) + (3aR,4R,4aR,7aS,8R,8aR)-8-Benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole-4-carbaldehyde → [(R)-((3aR,4R,4aR,7aR,8R,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl)-hydroxy-methyl]-phosphonic acid dibenzyl ester (444902-87-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(02)00354-4

Reference yield:

1D-6-O-benzyl-3-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol (291313-64-9) → [(R)-((3aR,4R,4aR,7aR,8R,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl)-hydroxy-methyl]-phosphonic acid dibenzyl ester (444902-87-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

2: BuLi / tetrahydrofuran / -78 °C

With n-butyllithium; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 1: Dess-Martin oxidation;

DOI:10.1016/S0040-4039(02)00354-4

Reference yield:

[(R)-((3aR,4R,4aR,7aR,8R,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl)-hydroxy-methyl]-phosphonic acid dibenzyl ester (444902-87-8) → [(R)-Hydroxy-((1R,2R,3S,4R,5R,6R)-2,3,4,5,6-pentahydroxy-cyclohexyl)-methyl]-phosphonic acid

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd(OH)2/C / 2-methyl-propan-2-ol / 20 °C / 760 Torr

2: HCl / H₂O / 20 °C

With hydrogenchloride; hydrogen; palladium dihydroxide; In water; tert-butyl alcohol;

DOI:10.1016/S0040-4039(02)00354-4

upstream raw materials:

Dibenzyl phosphite

1D-6-O-benzyl-3-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol