(1R)-2,3,5-tri-O-benzyl-4-O-formyl-D-arabinose-1-(dimethyl phosphonate)

Base Information

• Chemical Name: (1R)-2,3,5-tri-O-benzyl-4-O-formyl-D-arabinose-1-(dimethyl phosphonate)
• CAS No.: 158349-46-3
• Molecular Formula: C₂₉H₃₅O₉P
• Molecular Weight: 558.565
• Mol file: 158349-46-3.mol

Synonyms:(1R)-2,3,5-tri-O-benzyl-4-O-formyl-D-arabinose-1-(dimethyl phosphonate)

Chemical Property of (1R)-2,3,5-tri-O-benzyl-4-O-formyl-D-arabinose-1-(dimethyl phosphonate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-2,3,5-tri-O-benzyl-4-O-formyl-D-arabinose-1-(dimethyl phosphonate)

There total 1 articles about (1R)-2,3,5-tri-O-benzyl-4-O-formyl-D-arabinose-1-(dimethyl phosphonate) 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:

Dimethyl phosphite (868-85-9) + (2S,3R,4R)-2,3,5-tri-O-benzyl-4-O-formyl-pentanal (155931-84-3) → (1R)-2,3,5-tri-O-benzyl-4-O-formyl-D-arabinose-1-(dimethyl phosphonate) (158349-46-3) + (1S)-2,3,5-tri-O-benzyl-4-O-formyl-D-arabinose 1-(dimethyl phosphonate) (158349-45-2)

Guidance literature:

With titanium(IV) isopropylate; (R)-3,3'-diiodo-2,2'-dihydroxy-1,1'-binaphthyl; Cinchonidine; In toluene; at 0 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ja305104b

Reference yield: 47.0%

(1R)-2,3,5-tri-O-benzyl-4-O-formyl-D-arabinose-1-(dimethyl phosphonate) (158349-46-3) → (2S,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxy-2-methoxy-1,2-oxaphosphinane-2-oxide (158414-25-6) + (2R,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxy-2-methoxy-1,2-oxaphosphinane-2-oxide (158414-26-7)

Guidance literature:

With sodium hexamethyldisilazane; In methanol; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ja305104b

Reference yield:

(1R)-2,3,5-tri-O-benzyl-4-O-formyl-D-arabinose-1-(dimethyl phosphonate) (158349-46-3) → (2S,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2sulfido-1,2-oxaphosphinan-3-yl acetate (1384982-14-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hexamethyldisilazane / methanol / 24 h / 20 °C / Inert atmosphere

2: iodine / 7.5 h / 20 °C / Inert atmosphere

3: Lawessons reagent / toluene / 24 h / 70 °C / Inert atmosphere

With Lawessons reagent; iodine; sodium hexamethyldisilazane; In methanol; toluene;

DOI:10.1021/ja305104b

upstream raw materials:

Dimethyl phosphite

(2S,3R,4R)-2,3,5-tri-O-benzyl-4-O-formyl-pentanal

Downstream raw materials:

(2R,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(((2S,3S,4aR,5R,7S,8S,8aR)-8-hydroxy-2,3,7-trimethoxy-2,3-dimethylhexahydro-2Hpyrano[3,4-b][1,4]dioxin-5-yl)methoxy)-2-oxido-1,2-oxaphosphinan-3-yl acetate

C₅₆H₅₅O₁₆P

(2S,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-oxido-2-(((2R,3R,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)-1,2-oxaphosphinan-3-yl acetate

(2S,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(((2S,3R,4aR,5R,7S,8S,8aR)-8-hydroxy-2,3,7-trimethoxy-2,3-dimethylhexahydro-2Hpyrano[3,4-b][1,4]dioxin-5-yl)methoxy)-2-oxido-1,2-oxaphosphinan-3-yl acetate