(3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Base Information

Chemical Name:(3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
CAS No.:866605-96-1
Molecular Formula:C₃₀H₃₇ClO₇Si
Molecular Weight:573.158
Hs Code.:

Synonyms:(3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

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Chemical Property of (3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

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Technology Process of (3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

There total 1 articles about (3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 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:

: 67-56-1
methanol

: 866605-95-0
(5-bromo-2-chlorobenzyloxy)(tert-butyl)diphenylsilane

: 32469-28-6,55515-28-1,55515-29-2,32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 866605-96-1
(3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: (5-bromo-2-chlorobenzyloxy)(tert-butyl)diphenylsilane; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 5h;

methanol; With methanesulfonic acid; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1016/j.bmc.2014.04.036

Reference yield:

: 866605-96-1
(3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

: 1621966-46-8
C₄₄H₄₈ClN₃O₁₁Si

Guidance literature:: Multi-step reaction with 4 steps

1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C

2: pyridine; dmap / chloroform / 20 °C

3: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

4: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

With pyridine; triethylsilane; dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; chloroform; 4: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2014.04.036

Reference yield:

: 866605-96-1
(3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

: 1613149-87-3
C₂₈H₃₀ClN₃O₁₁

Guidance literature:: Multi-step reaction with 5 steps

1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C

2: pyridine; dmap / chloroform / 20 °C

3: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

4: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

5: tetrabutyl ammonium fluoride / tetrahydrofuran

With pyridine; triethylsilane; dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; chloroform; 4: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2014.04.036