methyl 4-<<(1S,2S)-(2,4/3)-2,3,4-tetrahydroxy-5-(hydroxymethyl)-5-cyclohexen-1-yl>amino>-4-deoxy-α-D-galactopyranoside

Base Information

• Chemical Name: methyl 4-<<(1S,2S)-(2,4/3)-2,3,4-tetrahydroxy-5-(hydroxymethyl)-5-cyclohexen-1-yl>amino>-4-deoxy-α-D-galactopyranoside
• CAS No.: 89920-25-2
• Molecular Formula: C₁₄H₂₅NO₉
• Molecular Weight: 351.354

Synonyms:methyl 4-<<(1S,2S)-(2,4/3)-2,3,4-tetrahydroxy-5-(hydroxymethyl)-5-cyclohexen-1-yl>amino>-4-deoxy-α-D-galactopyranoside

Chemical Property of methyl 4-<<(1S,2S)-(2,4/3)-2,3,4-tetrahydroxy-5-(hydroxymethyl)-5-cyclohexen-1-yl>amino>-4-deoxy-α-D-galactopyranoside

Chemical Property:

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Technology Process of methyl 4-<<(1S,2S)-(2,4/3)-2,3,4-tetrahydroxy-5-(hydroxymethyl)-5-cyclohexen-1-yl>amino>-4-deoxy-α-D-galactopyranoside

There total 7 articles about methyl 4-<<(1S,2S)-(2,4/3)-2,3,4-tetrahydroxy-5-(hydroxymethyl)-5-cyclohexen-1-yl>amino>-4-deoxy-α-D-galactopyranoside 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: 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

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:

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

Methyl-4-amino-4-deoxy-α-D-glucopyranoside

DL-3,4-di-O-Acetyl-1,2-anhydro-(1,2,3/4)-5-benzoyloxymethyl-5-cyclohexene-1,2,3,4-tetrol

valienamine

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