(1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol

Base Information

Chemical Name:(1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol
CAS No.:140926-92-7
Molecular Formula:C₆₂H₆₄O₁₁
Molecular Weight:985.184
Hs Code.:

Synonyms:(1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol

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Chemical Property of (1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol

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Technology Process of (1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol

There total 5 articles about (1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol 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: 84.0%

: 140926-91-6
(1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-6,6-dichloro-5-oxo-1,2,3,4-cyclohexanetetrol

: 140926-92-7
(1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 100 ℃; for 1h;
DOI:10.1021/jo00039a026

Reference yield:

: 148968-90-5
2,3,6-tris-O-(phenylmethyl)-4-O-[2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-glucopyranosyl]-D-glucopyranoside

: 140926-92-7
(1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / Ac₂O, DMSO / 20 h / Ambient temperature

2: 94 percent / LDA / tetrahydrofuran / 1 h / -75 - -70 °C

3: 87 percent / NaBH₄ / bis-(2-methoxy-ethyl) ether / Ambient temperature

4: 1) trifluoroacetic anhydride, DMSO, 2) Et₃N / 1) CH₂Cl₂, below -65 deg C, 1 h, 2a) CH₂Cl₂, below -65 deg C, 15 min, 2b) to 0 deg C

5: 84 percent / Bu₃SnH, AIBN / toluene / 1 h / 100 °C

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; acetic anhydride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; lithium diisopropyl amide; In tetrahydrofuran; diethylene glycol dimethyl ether; toluene;
DOI:10.1021/jo00039a026

Reference yield:

: 140926-89-2
2,3,6-Tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-C-(dichloromethyl)-α-D-glucopyranose

: 140926-92-7
(1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / NaBH₄ / bis-(2-methoxy-ethyl) ether / Ambient temperature

2: 1) trifluoroacetic anhydride, DMSO, 2) Et₃N / 1) CH₂Cl₂, below -65 deg C, 1 h, 2a) CH₂Cl₂, below -65 deg C, 15 min, 2b) to 0 deg C

3: 84 percent / Bu₃SnH, AIBN / toluene / 1 h / 100 °C

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In diethylene glycol dimethyl ether; toluene;
DOI:10.1021/jo00039a026