(5R)-3,6-di-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-glucofuranose

Base Information

Chemical Name:(5R)-3,6-di-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-glucofuranose
CAS No.:219901-09-4
Molecular Formula:C₂₅H₃₃O₈P
Molecular Weight:492.506
Hs Code.:

Synonyms:(5R)-3,6-di-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-glucofuranose

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Chemical Property of (5R)-3,6-di-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-glucofuranose

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Technology Process of (5R)-3,6-di-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-glucofuranose

There total 5 articles about (5R)-3,6-di-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-glucofuranose 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: 50.0%

: Oxalic acid 2-benzyloxy-1-((3aR,5S,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-1-(dimethoxy-phosphoryl)-ethyl ester methyl ester

: 219901-09-4
(5R)-3,6-di-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-glucofuranose

: 220204-94-4
(5S)-3,6-di-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-β-L-idofuranose

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃;
DOI:10.1016/S0008-6215(03)00235-0

Reference yield:

: 3,6-di-O-benzyl-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-xylo-hexofuranose

: 219901-09-4
(5R)-3,6-di-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: DMAP / acetonitrile / 0.5 h / 0 °C

2: 50 percent / Bu₃SnH; AIBN / toluene / 80 °C

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; acetonitrile;
DOI:10.1016/S0008-6215(03)00235-0

Reference yield:

: 59541-28-5
3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranose-5-ulose

: 219901-09-4
(5R)-3,6-di-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-glucofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: 43 percent / DBU / 0.5 h / 0 °C

2: 1.) monomethyl oxalyl chloride, DMAP; 2.) Bu₃SnH, AIBN / 1.) MeCN, 0 degC, 30 min; 2.) toluene, 80 degC, 6 h

With monomethyl oxalyl chloride; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene;
DOI:10.3987/com-98-s(h)53