methyl 3-[5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-3-deoxy-α-D-glucopyranoside

Base Information

Chemical Name:methyl 3-[5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-3-deoxy-α-D-glucopyranoside
CAS No.:1332641-43-6
Molecular Formula:C₁₄H₂₅NO₉
Molecular Weight:351.354
Hs Code.:

Synonyms:methyl 3-[5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-3-deoxy-α-D-glucopyranoside

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Chemical Property of methyl 3-[5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-3-deoxy-α-D-glucopyranoside

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Technology Process of methyl 3-[5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-3-deoxy-α-D-glucopyranoside

There total 4 articles about methyl 3-[5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-3-deoxy-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: 40.0%

: 1332641-37-8
methyl 3-[2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-4,6-Obenzylidene-3-deoxy-α-D-glucopyranoside

: 1332641-43-6
methyl 3-[5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-3-deoxy-α-D-glucopyranoside

Guidance literature:: With ammonia; sodium; In tetrahydrofuran; methanol; at -78 ℃; for 0.116667h; Inert atmosphere;
DOI:10.1016/j.bmcl.2011.07.046

Reference yield:

: 99695-34-8
(1R,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol

: 1332641-43-6
methyl 3-[5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-3-deoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: carbon tetrabromide / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: tetrabutylammomium bromide / dichloromethane / 10 h / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 46 h / 75 °C / Inert atmosphere

4.1: ammonia; sodium / tetrahydrofuran; methanol / 0.12 h / -78 °C / Inert atmosphere

With carbon tetrabromide; tetrabutylammomium bromide; ammonia; sodium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1.1: Appel reaction;
DOI:10.1016/j.bmcl.2011.07.046

Reference yield:

: 1332641-33-4
2,3,4,6-tetra-O-benzyl-5a-carba-α-D-xylo-hex-5(5a)-enopyranosyl bromide

: 1332641-43-6
methyl 3-[5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-3-deoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: tetrabutylammomium bromide / dichloromethane / 10 h / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine / acetonitrile / 46 h / 75 °C / Inert atmosphere

3: ammonia; sodium / tetrahydrofuran; methanol / 0.12 h / -78 °C / Inert atmosphere

With tetrabutylammomium bromide; ammonia; sodium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1016/j.bmcl.2011.07.046