methyl 4-deoxy-4-<(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 4-deoxy-4-<(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-α-D-glucopyranoside
• CAS No.: 89859-74-5
• Molecular Formula: C₁₄H₂₅NO₉
• Molecular Weight: 351.354

Synonyms:methyl 4-deoxy-4-<(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-α-D-glucopyranoside

Chemical Property of methyl 4-deoxy-4-<(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-α-D-glucopyranoside

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Technology Process of methyl 4-deoxy-4-<(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-α-D-glucopyranoside

There total 9 articles about methyl 4-deoxy-4-<(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-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: 89.0%

methyl 2,3,6,4',5',6',7'-hepta-O-acetyl-4-deoxy-4-<(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenylamino>-α-D-glucopyranoside (101072-28-0,101144-21-2,101144-23-4,101144-25-6,101400-19-5,101400-21-9) → methyl 4-deoxy-4-<(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-α-D-glucopyranoside (89859-74-5)

Guidance literature:

With sodium methylate; In methanol; for 1h; Ambient temperature;

DOI:10.1016/0008-6215(92)84132-C

Reference yield: 7.0%

valienamine (38231-86-6) + methyl 6-O-acetyl-2,3-cyclohexylidene-α-D-xylo-hexopyranosid-4-ulose (89859-46-1) → methyl 4-<<(1S,2S)-(2,4/3)-2,3,4-tetrahydroxy-5-(hydroxymethyl)-5-cyclohexen-1-yl>amino>-4-deoxy-α-D-glucopyranoside (89859-74-5) + methyl 4-<<(1S,2S)-(2,4/3)-2,3,4-tetrahydroxy-5-(hydroxymethyl)-5-cyclohexen-1-yl>amino>-4-deoxy-α-D-galactopyranoside (89920-25-2)

Guidance literature:

With hydrogenchloride; NaBH₄CN; In N,N-dimethyl-formamide; at 60 - 70 ℃; for 18h;

DOI:10.1021/jm00156a023

Reference yield:

Benzoic acid 4,5,6-triacetoxy-3-((2S,3R,4S,5R,6S)-4,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-3-ylamino)-cyclohex-1-enylmethyl ester (141232-09-9) → (1S,2R,3S,6R)-6-((2S,3S,4S,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-ylamino)-4-hydroxymethyl-cyclohex-4-ene-1,2,3-triol (89859-74-5,89920-25-2,101144-22-3,101144-24-5,141316-51-0) + (1R,2S,3R,6S)-6-((2S,3S,4S,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-ylamino)-4-hydroxymethyl-cyclohex-4-ene-1,2,3-triol (89859-74-5,89920-25-2,101144-22-3,101144-24-5,141316-51-0)

Guidance literature:

With sodium methylate; In methanol; for 0.666667h; Ambient temperature;

DOI:10.1016/S0008-6215(00)90465-8

upstream raw materials:

methyl 2,3,6,4',5',6',7'-hepta-O-acetyl-4-deoxy-4-<(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenylamino>-α-D-glucopyranoside

DL-4,7:5,6-di-O-isopropylidene-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenylamine

Methyl 3,4-anhydro-α-D-galactopyranoside

Benzoic acid 4,5,6-triacetoxy-3-((2S,3R,4S,5R,6S)-4,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-3-ylamino)-cyclohex-1-enylmethyl ester

Downstream raw materials:

methyl 2,3,6,4',5',6',7'-hepta-O-acetyl-4-deoxy-4-<(1S)-(1,4,6/5)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenylamino>-α-D-glucopyranoside

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