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

Base Information

Chemical Name:((2S,3R,4S,5S,6R)-3-acetoxy-4,5-bis(benzyloxy)-2-methoxy-2-oxido-1,2-oxaphosphinan-6yl)methyl acetate
CAS No.:1384982-09-5
Molecular Formula:C₂₄H₂₉O₉P
Molecular Weight:492.463
Hs Code.:

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

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

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

There total 3 articles about ((2S,3R,4S,5S,6R)-3-acetoxy-4,5-bis(benzyloxy)-2-methoxy-2-oxido-1,2-oxaphosphinan-6yl)methyl 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: 90.0%

: 1384982-08-4
(2S,3S,4S,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-methoxy-2-oxido-1,2-oxaphosphinan-3yl acetate

: 108-24-7
acetic anhydride

: 1384982-09-5
((2S,3R,4S,5S,6R)-3-acetoxy-4,5-bis(benzyloxy)-2-methoxy-2-oxido-1,2-oxaphosphinan-6yl)methyl acetate

Guidance literature:: With trifluoroacetic acid; at 20 ℃; for 6h; Inert atmosphere;
DOI:10.1021/jo400864s

Reference yield: 74.0%

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

: 108-24-7
acetic anhydride

: 1384982-09-5
((2S,3R,4S,5S,6R)-3-acetoxy-4,5-bis(benzyloxy)-2-methoxy-2-oxido-1,2-oxaphosphinan-6yl)methyl acetate

Guidance literature:: With iodine; at 20 ℃; Inert atmosphere;
DOI:10.1021/ja305104b

Reference yield:

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

: 1384982-09-5
((2S,3R,4S,5S,6R)-3-acetoxy-4,5-bis(benzyloxy)-2-methoxy-2-oxido-1,2-oxaphosphinan-6yl)methyl acetate

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