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

Base Information

Chemical Name:(2S,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxy-2-methoxy-1,2-oxaphosphinane-2-oxide
CAS No.:158414-25-6
Molecular Formula:C₂₇H₃₁O₇P
Molecular Weight:498.513
Hs Code.:

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

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

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

There total 3 articles about (2S,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxy-2-methoxy-1,2-oxaphosphinane-2-oxide 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: 47.0%

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

: 158414-25-6
(2S,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)-3-hydroxy-2-methoxy-1,2-oxaphosphinane-2-oxide

Guidance literature:: With sodium hexamethyldisilazane; In methanol; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1021/ja305104b

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 158414-25-6
(2S,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxy-2-methoxy-1,2-oxaphosphinane-2-oxide

Guidance literature:: Multi-step reaction with 3 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

With titanium(IV) isopropylate; sodium periodate; osmium(VIII) oxide; 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:

: 155931-84-3
(2S,3R,4R)-2,3,5-tri-O-benzyl-4-O-formyl-pentanal

: 158414-25-6
(2S,3R,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxy-2-methoxy-1,2-oxaphosphinane-2-oxide

Guidance literature:: Multi-step reaction with 2 steps

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

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

With titanium(IV) isopropylate; sodium hexamethyldisilazane; (R)-3,3'-diiodo-2,2'-dihydroxy-1,1'-binaphthyl; Cinchonidine; In methanol; toluene;
DOI:10.1021/ja305104b