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

Base Information

• Chemical Name: (2R,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2sulfido-1,2-oxaphosphinan-3-yl acetate
• CAS No.: 1384982-15-3
• Molecular Formula: C₂₉H₃₃O₇PS
• Molecular Weight: 556.617
• Mol file: 1384982-15-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

Reference yield:

(1R)-2,3,5-tri-O-benzyl-4-O-formyl-D-arabinose-1-(dimethyl phosphonate) (158349-46-3) → (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:

Multi-step reaction with 3 steps

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

2: iodine / 20 °C / Inert atmosphere

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

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

DOI:10.1021/ja305104b

Reference yield:

(2R,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxy-2-methoxy-1,2-oxaphosphinane-2-oxide (158414-26-7) → (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:

Multi-step reaction with 2 steps

1: iodine / 20 °C / Inert atmosphere

2: Lawessons reagent / toluene / 70 °C / Inert atmosphere

With Lawessons reagent; iodine; In toluene;

DOI:10.1021/ja305104b

upstream raw materials:

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

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

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

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

(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