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

Base Information

• Chemical Name: (2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2-oxido-1,2-oxaphosphinan-3yl acetate
• CAS No.: 1384982-10-8
• Molecular Formula: C₂₉H₃₃O₈P
• Molecular Weight: 540.55
• Mol file: 1384982-10-8.mol

Synonyms:(2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2-oxido-1,2-oxaphosphinan-3yl acetate

Chemical Property of (2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2-oxido-1,2-oxaphosphinan-3yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2-oxido-1,2-oxaphosphinan-3yl acetate

There total 2 articles about (2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2-oxido-1,2-oxaphosphinan-3yl acetate 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: 64.0%

(2R,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxy-2-methoxy-1,2-oxaphosphinane-2-oxide (158414-26-7) + acetic anhydride (108-24-7) → (2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2-oxido-1,2-oxaphosphinan-3yl acetate (1384982-10-8)

Guidance literature:

With iodine; at 20 ℃; Inert atmosphere;

DOI:10.1021/ja305104b

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → (2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2-oxido-1,2-oxaphosphinan-3yl acetate (1384982-10-8)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium periodate; osmium(VIII) oxide / diethyl ether; water / 6 h / Inert atmosphere

2: titanium(IV) isopropylate; (R)-3,3'-diiodo-2,2'-dihydroxy-1,1'-binaphthyl; Cinchonidine / toluene / 0 °C / Inert atmosphere

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

4: iodine / 20 °C / Inert atmosphere

With titanium(IV) isopropylate; sodium periodate; osmium(VIII) oxide; iodine; sodium hexamethyldisilazane; (R)-3,3'-diiodo-2,2'-dihydroxy-1,1'-binaphthyl; Cinchonidine; In methanol; diethyl ether; water; toluene;

DOI:10.1021/ja305104b

Reference yield: 68.0%

(2R,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2-oxido-1,2-oxaphosphinan-3yl acetate (1384982-10-8) → (2R,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2sulfido-1,2-oxaphosphinan-3-yl acetate (1384982-15-3)

Guidance literature:

With Lawessons reagent; In toluene; at 70 ℃; Inert atmosphere;

DOI:10.1021/ja305104b

upstream raw materials:

(2R,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxy-2-methoxy-1,2-oxaphosphinane-2-oxide

acetic anhydride

3,4,6-tri-O-benzyl-D-glucal

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

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