Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester
CAS No.:390400-37-0
Molecular Formula:C₄₄H₄₇Cl₂NO₁₅S
Molecular Weight:932.827
Hs Code.:

Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester

Synonyms:Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester

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Chemical Property of Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester

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Technology Process of Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester

There total 6 articles about Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester 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: 73.0%

: 115533-35-2
ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 251348-05-7
2,6-di-O-acetyl-3,4-di-O-chloroacetyl-α-D-galactopyranosyl chloride

: 390400-37-0
Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: With 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate; In dichloromethane; at -20 - 0 ℃; for 5h;
DOI:10.1016/S0960-894X(01)00550-9

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 390400-37-0
Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / p-TsOH / acetonitrile / 20 °C

2: 74 percent / NaH / dimethylformamide / 2 h / 0 °C

3: 76 percent / NaBH₃CN; HCl; MS-3 A / diethyl ether / 1 h / 0 - 5 °C

4: 73 percent / AgOTf; 2,4,6-collidine; MS-4A / CH₂Cl₂ / 5 h / -20 - 0 °C

With 2,4,6-trimethyl-pyridine; hydrogenchloride; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0960-894X(01)00550-9

Reference yield:

: 99409-32-2
ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 390400-37-0
Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / MeONa / methanol / 0.33 h / 20 °C

2: 87 percent / p-TsOH / acetonitrile / 20 °C

3: 74 percent / NaH / dimethylformamide / 2 h / 0 °C

4: 76 percent / NaBH₃CN; HCl; MS-3 A / diethyl ether / 1 h / 0 - 5 °C

5: 73 percent / AgOTf; 2,4,6-collidine; MS-4A / CH₂Cl₂ / 5 h / -20 - 0 °C

With 2,4,6-trimethyl-pyridine; hydrogenchloride; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0960-894X(01)00550-9