(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

Base Information

Chemical Name:(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
CAS No.:1384982-31-3
Molecular Formula:C₅₆H₆₁O₁₃P
Molecular Weight:973.066
Hs Code.:

(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

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Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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:

: 53008-65-4,641635-63-4
methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

: triethylammonium (2S,3R,4S,5S,6R)-2-borane-3-acetoxy-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-1,2-oxaphosphinan-2-olate

: 1384982-31-3
(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

Guidance literature:: methyl 2,3,4-tri-O-benzyl-D-glucopyranoside; triethylammonium (2S,3R,4S,5S,6R)-2-borane-3-acetoxy-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-1,2-oxaphosphinan-2-olate; With dmap; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; Inert atmosphere; Molecular sieve;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 0.166667h; Inert atmosphere;
DOI:10.1021/ja305104b

Reference yield:

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

: 1384982-31-3
(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

Guidance literature:: Multi-step reaction with 3 steps

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

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

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

3.2: 0.17 h / 20 °C / Inert atmosphere

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

: 1384982-31-3
(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

Guidance literature:: Multi-step reaction with 2 steps

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

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

2.2: 0.17 h / 20 °C / Inert atmosphere

With dmap; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; thiophenol; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;
DOI:10.1021/ja305104b