methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)-α-D-glucopyranoside
CAS No.:244286-71-3
Molecular Formula:C₅₅H₅₈O₁₀
Molecular Weight:879.06
Hs Code.:

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)-α-D-glucopyranoside

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Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)-α-D-glucopyranoside

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Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)-α-D-glucopyranoside

There total 8 articles about methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)-α-D-glucopyranoside 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: 91.0%

: 244286-80-4
methyl 2,3,6,2',3',4'-hexa-O-benzyl-6'-deoxy-6'-iodo-α-D-maltoside

: 244286-71-3
methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)-α-D-glucopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;
DOI:10.1002/anie.201405008

Reference yield:

: 244286-79-1
methyl 2,3,6,2',3',4'-hexa-O-benzyl-α-D-maltoside

: 244286-71-3
methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / I₂; PhP₃; imidazole / toluene / 1 h / 70 °C

2: 52 percent / DBU / tetrahydrofuran / 42 h / Heating

With 1H-imidazole; iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; toluene; 1: Iodination / 2: Dehydroiodination;

Reference yield:

: 3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4,20880-60-8
1,2,3,6,2',3',4',6'-octa-O-acetylmaltose

: 244286-71-3
methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: BF₃*OEt₂ / 2 h / 20 °C

2: NaOMe / methanol

3: 48 percent / camphorsulfonic acid / dimethylformamide / 1 h / 60 °C / 1 Torr

4: 55 percent / NaH / dimethylformamide / 1 h / 20 °C

5: 94 percent / LiAlH₄; AlCl₃ / CH₂Cl₂; diethyl ether / 1 h / 50 °C

6: 73 percent / N-chlorosuccinimide / 1 h / 20 °C

7: 93 percent / I₂; PhP₃; imidazole / toluene / 1 h / 70 °C

8: 52 percent / DBU / tetrahydrofuran / 42 h / Heating

With 1H-imidazole; N-chloro-succinimide; lithium aluminium tetrahydride; aluminium trichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; iodine; sodium methylate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 1: thioglycosylation / 2: Deacetylation / 3: Condensation / 4: benzylation / 5: Ring cleavage / 6: Substitution / 7: Iodination / 8: Dehydroiodination;