3,4,5,7-tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-D-xylo-2,6-heptodiulose

Base Information

Chemical Name:3,4,5,7-tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-D-xylo-2,6-heptodiulose
CAS No.:115250-32-3
Molecular Formula:C₃₇H₄₁O₉P
Molecular Weight:660.701
Hs Code.:

Synonyms:3,4,5,7-tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-D-xylo-2,6-heptodiulose

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Chemical Property of 3,4,5,7-tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-D-xylo-2,6-heptodiulose

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Technology Process of 3,4,5,7-tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-D-xylo-2,6-heptodiulose

There total 4 articles about 3,4,5,7-tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-D-xylo-2,6-heptodiulose 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:

: 115250-30-1,115305-00-5
((3S,4S,5R,6R)-3,4,5,7-Tetrakis-benzyloxy-2,6-dihydroxy-heptyl)-phosphonic acid dimethyl ester

: 115250-32-3
3,4,5,7-tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-D-xylo-2,6-heptodiulose

Guidance literature:: With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; Yield given. Multistep reaction; 1) CH₂Cl₂, -75 to -65 deg C, 1 h, 2a) CH₂Cl₂, -75 to -65 deg C, 2b) to 0 deg C;
DOI:10.1021/jo00039a026

Reference yield:

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 115250-32-3
3,4,5,7-tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-D-xylo-2,6-heptodiulose

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - -70 °C

2: 94 percent / NaBH₄ / tetrahydrofuran / 18 h / Ambient temperature

3: 1) trifluoroacetic anhydride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -75 to -65 deg C, 1 h, 2a) CH₂Cl₂, -75 to -65 deg C, 2b) to 0 deg C

With sodium tetrahydroborate; n-butyllithium; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; hexane;
DOI:10.1021/jo00039a026

Reference yield:

: 140926-87-0
3,4,5,7-Tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-α-D-gluco-2-heptulopyranose

: 115250-32-3
3,4,5,7-tetra-O-benzyl-1-deoxy-1-(dimethoxyphosphoryl)-D-xylo-2,6-heptodiulose

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / NaBH₄ / tetrahydrofuran / 18 h / Ambient temperature

2: 1) trifluoroacetic anhydride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -75 to -65 deg C, 1 h, 2a) CH₂Cl₂, -75 to -65 deg C, 2b) to 0 deg C

With sodium tetrahydroborate; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran;
DOI:10.1021/jo00039a026