Ethyl 6,7-O-di-O-benzyl-2,3-O-isopropylidene-4-O-(4-methoxy)benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

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Chemical Name:Ethyl 6,7-O-di-O-benzyl-2,3-O-isopropylidene-4-O-(4-methoxy)benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside
CAS No.:140231-91-0
Molecular Formula:C₃₄H₄₂O₇S
Molecular Weight:594.769
Hs Code.:

Synonyms:Ethyl 6,7-O-di-O-benzyl-2,3-O-isopropylidene-4-O-(4-methoxy)benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

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Chemical Property of Ethyl 6,7-O-di-O-benzyl-2,3-O-isopropylidene-4-O-(4-methoxy)benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

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Technology Process of Ethyl 6,7-O-di-O-benzyl-2,3-O-isopropylidene-4-O-(4-methoxy)benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

There total 14 articles about Ethyl 6,7-O-di-O-benzyl-2,3-O-isopropylidene-4-O-(4-methoxy)benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside 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: 82.0%

: 100-39-0
benzyl bromide

: 286845-67-8
ethyl 7-O-benzyl-2,3-O-isopropylidene-4-O-p-methoxybenzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

: 140231-91-0
Ethyl 6,7-O-di-O-benzyl-2,3-O-isopropylidene-4-O-(4-methoxy)benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: ethyl 7-O-benzyl-2,3-O-isopropylidene-4-O-p-methoxybenzyl-1-thio-L-glycero-α-D-manno-heptopyranoside; With sodium hydride; In N,N-dimethyl-formamide; Petroleum ether; for 2h;

benzyl bromide; In N,N-dimethyl-formamide; Petroleum ether; at 20 ℃; for 2h;
DOI:10.1016/S0957-4166(99)00554-6

Reference yield:

: 116302-67-1
2,3,4,6,7-penta-O-acetyl-L-glycero-α-D-manno-heptopyranosyl bromide

: 140231-91-0
Ethyl 6,7-O-di-O-benzyl-2,3-O-isopropylidene-4-O-(4-methoxy)benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) KOtBu / 1.) MeOH, 2.) ethyl acetate, 45 min, room temperture

2: camphorsulfonic acid / acetone / 18 h / Ambient temperature

3: 73 percent / NaH, (n-Bu)4NI / dimethylformamide / 1.5 h / Ambient temperature

4: 65 percent / aq. HOAc / 15 h / Ambient temperature

5: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) 3 h, room temperature

With camphor-10-sulfonic acid; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(01)88191-6

Reference yield:

: 140209-72-9
(2R,3S,4S,5S,6R)-2-((S)-1,2-Dihydroxy-ethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 140231-91-0
Ethyl 6,7-O-di-O-benzyl-2,3-O-isopropylidene-4-O-(4-methoxy)benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: camphorsulfonic acid / acetone / 18 h / Ambient temperature

2: 73 percent / NaH, (n-Bu)4NI / dimethylformamide / 1.5 h / Ambient temperature

3: 65 percent / aq. HOAc / 15 h / Ambient temperature

4: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) 3 h, room temperature

With camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(01)88191-6