(E)-ethyl (ethyl 2,3,4-tri-O-benzyl-6,7-dideoxy-1,5-dithio-α-D-gluco-oct-6-enopyranosid)-uronate

Base Information

Chemical Name:(E)-ethyl (ethyl 2,3,4-tri-O-benzyl-6,7-dideoxy-1,5-dithio-α-D-gluco-oct-6-enopyranosid)-uronate
CAS No.:313046-41-2
Molecular Formula:C₃₃H₃₈O₅S₂
Molecular Weight:578.794
Hs Code.:

Synonyms:(E)-ethyl (ethyl 2,3,4-tri-O-benzyl-6,7-dideoxy-1,5-dithio-α-D-gluco-oct-6-enopyranosid)-uronate

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Chemical Property of (E)-ethyl (ethyl 2,3,4-tri-O-benzyl-6,7-dideoxy-1,5-dithio-α-D-gluco-oct-6-enopyranosid)-uronate

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Technology Process of (E)-ethyl (ethyl 2,3,4-tri-O-benzyl-6,7-dideoxy-1,5-dithio-α-D-gluco-oct-6-enopyranosid)-uronate

There total 8 articles about (E)-ethyl (ethyl 2,3,4-tri-O-benzyl-6,7-dideoxy-1,5-dithio-α-D-gluco-oct-6-enopyranosid)-uronate 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:

: 10227-18-6
1,2,3,4,6-penta-O-acetyl-5-thio-α-D-glucopyranoside

: 313046-41-2
(E)-ethyl (ethyl 2,3,4-tri-O-benzyl-6,7-dideoxy-1,5-dithio-α-D-gluco-oct-6-enopyranosid)-uronate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 45 percent / BF₃*Et₂O / CH₂Cl₂ / 6 h / 20 °C

2.1: NaOMe / methanol / 0.5 h / 20 °C

3.1: 86 percent / p-toluenesulfonic acid / acetonitrile / 20 h / 20 °C

4.1: NaH / dimethylformamide / 0.17 h / 0 °C

4.2: 92 percent / dimethylformamide / 2 h

5.1: 86 percent / Me₃N*BH₃; AlCl₃; molecular sieves / CH₂Cl₂; diethyl ether / 0.5 h / 0 °C

6.1: DMSO; oxalyl chloride / CH₂Cl₂ / 0.25 h / -78 °C

7.1: CH₂Cl₂ / 1 h / 20 °C

With aluminium trichloride; molecular sieve; oxalyl dichloride; trimethylamine-borane; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 6.1: Swern oxidation / 7.1: Wittig olefination;
DOI:10.1021/ja002038h

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 313046-41-2
(E)-ethyl (ethyl 2,3,4-tri-O-benzyl-6,7-dideoxy-1,5-dithio-α-D-gluco-oct-6-enopyranosid)-uronate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 86 percent / p-toluenesulfonic acid / acetonitrile / 20 h / 20 °C

2.1: NaH / dimethylformamide / 0.17 h / 0 °C

2.2: 92 percent / dimethylformamide / 2 h

3.1: 86 percent / Me₃N*BH₃; AlCl₃; molecular sieves / CH₂Cl₂; diethyl ether / 0.5 h / 0 °C

4.1: DMSO; oxalyl chloride / CH₂Cl₂ / 0.25 h / -78 °C

5.1: CH₂Cl₂ / 1 h / 20 °C

With aluminium trichloride; molecular sieve; oxalyl dichloride; trimethylamine-borane; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 4.1: Swern oxidation / 5.1: Wittig olefination;
DOI:10.1021/ja002038h

Reference yield:

: 190649-80-0
ethyl 2,3,4,6-tetra-O-acetyl-1,5-dithio-α-D-glucopyranoside

: 313046-41-2
(E)-ethyl (ethyl 2,3,4-tri-O-benzyl-6,7-dideoxy-1,5-dithio-α-D-gluco-oct-6-enopyranosid)-uronate

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaOMe / methanol / 0.5 h / 20 °C

2.1: 86 percent / p-toluenesulfonic acid / acetonitrile / 20 h / 20 °C

3.1: NaH / dimethylformamide / 0.17 h / 0 °C

3.2: 92 percent / dimethylformamide / 2 h

4.1: 86 percent / Me₃N*BH₃; AlCl₃; molecular sieves / CH₂Cl₂; diethyl ether / 0.5 h / 0 °C

5.1: DMSO; oxalyl chloride / CH₂Cl₂ / 0.25 h / -78 °C

6.1: CH₂Cl₂ / 1 h / 20 °C

With aluminium trichloride; molecular sieve; oxalyl dichloride; trimethylamine-borane; sodium methylate; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 5.1: Swern oxidation / 6.1: Wittig olefination;
DOI:10.1021/ja002038h