(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

Base Information

• Chemical Name: (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
• CAS No.: 1384982-28-8
• Molecular Formula: C₄₁H₅₃O₁₅P
• Molecular Weight: 816.837
• Mol file: 1384982-28-8.mol

Synonyms:(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

Chemical Property of (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

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-(((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

There total 7 articles about (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 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: 80.0%

(2S,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-borane-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)-1,2-oxaphosphinan-3-yl acetate → (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 (1384982-28-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1021/ja305104b

Reference yield:

(2R,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2sulfido-1,2-oxaphosphinan-3-yl acetate (1384982-15-3) → (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 (1384982-28-8)

Guidance literature:

Multi-step reaction with 4 steps

1: dimethylsulfide borane complex / tetrahydrofuran / 3.5 h / Inert atmosphere

2: thiophenol / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

3: dmap; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; toluene / 3.5 h / 20 °C / Inert atmosphere; Molecular sieve

4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

With dmap; dimethylsulfide borane complex; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; thiophenol; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja305104b

Reference yield:

(2S,3R,4S,5S,6R)-2-boranyl-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-1,2-oxaphosphinan-3-yl acetate → (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 (1384982-28-8)

Guidance literature:

Multi-step reaction with 3 steps

1: thiophenol / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

2: dmap; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; toluene / 3.5 h / 20 °C / Inert atmosphere; Molecular sieve

3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

With dmap; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; thiophenol; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 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

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

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

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