methyl 4-deoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-2,6-di-O-p-tolylsulfonyl-α-D-glucopyranoside 4',7':5',6'-di-O-isopropylidene derivative

Base Information

Chemical Name:methyl 4-deoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-2,6-di-O-p-tolylsulfonyl-α-D-glucopyranoside 4',7':5',6'-di-O-isopropylidene derivative
CAS No.:139964-54-8
Molecular Formula:C₃₄H₄₅NO₁₃S₂
Molecular Weight:739.862
Hs Code.:

methyl 4-deoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-2,6-di-O-p-tolylsulfonyl-α-D-glucopyranoside 4',7':5',6'-di-O-isopropylidene derivative

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Chemical Property of methyl 4-deoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-2,6-di-O-p-tolylsulfonyl-α-D-glucopyranoside 4',7':5',6'-di-O-isopropylidene derivative

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Technology Process of methyl 4-deoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-2,6-di-O-p-tolylsulfonyl-α-D-glucopyranoside 4',7':5',6'-di-O-isopropylidene derivative

There total 5 articles about methyl 4-deoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-2,6-di-O-p-tolylsulfonyl-α-D-glucopyranoside 4',7':5',6'-di-O-isopropylidene derivative 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: 33.0%

: 131922-33-3,140148-04-5
methyl 4-deoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-α-D-glucopyranoside 4',7':5',6'-di-O-isopropylidene derivative

: 98-59-9
p-toluenesulfonyl chloride

: 131922-34-4,140148-05-6
methyl 4-deoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-6-O-p-tolylsulfonyl-α-D-glucopyranoside 4',7':5',6'-di-O-isopropylidene derivative

: 139964-54-8
methyl 4-deoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-2,6-di-O-p-tolylsulfonyl-α-D-glucopyranoside 4',7':5',6'-di-O-isopropylidene derivative

Guidance literature:: With pyridine; at 0 ℃; for 37h;
DOI:10.1016/0008-6215(92)80025-V

Reference yield:

: 132016-22-9
(1S,2R,9S,10S)-9-amino-4,4,12,12-tetramethyl-3,5,11,13-tetraoxatricyclo[8.3.0.0^2,7]tridec-7-ene

: 139964-54-8
methyl 4-deoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-2,6-di-O-p-tolylsulfonyl-α-D-glucopyranoside 4',7':5',6'-di-O-isopropylidene derivative

Guidance literature:: Multi-step reaction with 2 steps

1: 51 percent / propan-2-ol / 45 h / 120 °C

2: 33 percent / pyridine / 37 h / 0 °C

With pyridine; In isopropyl alcohol;
DOI:10.1016/0008-6215(92)80025-V

Reference yield:

: (1S)-(1,3/2,6)- and (1,3,6/2)-4-acetoxymethyl-1,2,3-tri-O-acetyl-6-azido-4-cyclohexene-1,2,3-triol

: 139964-54-8
methyl 4-deoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-2,6-di-O-p-tolylsulfonyl-α-D-glucopyranoside 4',7':5',6'-di-O-isopropylidene derivative

Guidance literature:: Multi-step reaction with 4 steps

1: 1) NaOMe, 2) p-toluenesulfonic acid monohydrate / 1) MeOH, r.t., 2 h, 2) DMF, r.t., 16 h

2: 97 percent / H₂S, 50percent aq. pyridine / 2 h / Ambient temperature

3: 51 percent / propan-2-ol / 45 h / 120 °C

4: 33 percent / pyridine / 37 h / 0 °C

With pyridine; hydrogen sulfide; sodium methylate; toluene-4-sulfonic acid; In isopropyl alcohol;
DOI:10.1016/0008-6215(92)80025-V