(3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose

Base Information

• Chemical Name: (3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose
• CAS No.: 190188-88-6
• Molecular Formula: C₂₃H₂₉NO₅Si
• Molecular Weight: 427.572

Synonyms:(3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose

Chemical Property of (3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose

Chemical Property:

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Technology Process of (3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose

There total 10 articles about (3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose 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%

N-methoxylamine hydrochloride (593-56-6) + 1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-β-D-arabino-hexopyran-3-ulose (149793-78-2) → (3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose (190188-88-6)

Guidance literature:

With pyridine; In dichloromethane; for 3h; Heating;

DOI:10.1021/jo000325y

Reference yield: 17.0%

(3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-2-O-(1'-ethoxy-2'-iodoethyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose (190188-91-1) → (3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose (190188-88-6) + (1R,2S,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxy)-4-(1-ethoxy-ethoxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-one O-methyl-oxime + (1R,2S,4S,7R,8S,9R)-8-(tert-Butyl-diphenyl-silanyloxy)-4-ethoxy-6-methoxy-3,11,12-trioxa-6-aza-tricyclo[7.2.1.02,7]dodecane

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tributyltin chloride; sodium cyanoborohydride; In tert-butyl alcohol; at 90 ℃; for 12h;

DOI:10.1021/jo000325y

Reference yield: 16.0%

Bromo-acetic acid (1R,2S,4S,5R)-2-(tert-butyl-diphenyl-silanyloxy)-3-[(Z)-methoxyimino]-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester (190188-89-7) → (3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose (190188-88-6) + Acetic acid (1R,2S,4S,5R)-2-(tert-butyl-diphenyl-silanyloxy)-3-[(Z)-methoxyimino]-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; Heating;

DOI:10.1016/S0040-4039(97)00460-7

upstream raw materials:

N-methoxylamine hydrochloride

1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-β-D-arabino-hexopyran-3-ulose

(3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-2-O-(1'-ethoxy-2'-iodoethyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose

Bromo-acetic acid (1R,2S,4S,5R)-2-(tert-butyl-diphenyl-silanyloxy)-3-[(Z)-methoxyimino]-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

Downstream raw materials:

(Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-2-O-(prop-2'-inyl)-β-D-arabino-hexopyranose

(3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-2-O-(1'-ethoxy-2'-iodoethyl)-3-deoxy-3-methoxyimine-β-D-arabino-hexopyranose

Bromo-acetic acid (1R,2S,4S,5R)-2-(tert-butyl-diphenyl-silanyloxy)-3-[(Z)-methoxyimino]-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

(3Z)-1,6-anhydro-4-O-(tert-butyldiphenylsilyl)-3-deoxy-3-methoxyimine-2-O-(2'-bromo-prop-2'-enyl)-β-D-arabino-hexopyranose

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