(2R,3R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2R,3R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol
CAS No.:128271-00-1
Molecular Formula:C₂₃H₃₀O₇
Molecular Weight:418.487
Hs Code.:

Synonyms:(2R,3R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

Chemical Property:

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Technology Process of (2R,3R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

There total 1 articles about (2R,3R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol 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:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 100-39-0
benzyl bromide

: 97-30-3
methyl-alpha-D-glucopyranoside

: 74-88-4
methyl iodide

: 128271-00-1
(2R,3R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

Guidance literature:: Yield given. Multistep reaction;
DOI:10.1021/jo00301a007

Reference yield:

: 128271-00-1
(2R,3R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

: (S)-N-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-Dihydroxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-2-(3,4-dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetamide

Guidance literature:: Multi-step reaction with 13 steps

3: OsO₄ / N,N'-bis(2,4,6-trimethylbenzyl)-(S,S)-1,2-diphenyl-1,2-diaminoethane / CH₂Cl₂ / -90 °C

6: H₂ / Pd(OH)2 on C / ethyl acetate / Ambient temperature

7: hydrochlorid acid / 0 °C

8: Et₃N, DMAP / CH₂Cl₂ / -60 °C

9: (n-Bu₄N)N₃ / CH₂Cl₂ / -78 deg C to room temperature

10: H₂ / Pd on C / ethyl acetate / Ambient temperature

12: 42 percent / potassium tert-butoxide / tetrahydrofuran / Heating

13: t-BuOK / tetrahydrofuran / Ambient temperature

With hydrogenchloride; dmap; osmium(VIII) oxide; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; potassium tert-butylate; hydrogen; tetrabutylammoniun azide; triethylamine; palladium on activated charcoal; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1021/jo00301a007

Reference yield:

: 128271-00-1
(2R,3R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol

: 128271-11-4,128385-71-7
(S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide

Guidance literature:: Multi-step reaction with 12 steps

3: OsO₄ / N,N'-bis(2,4,6-trimethylbenzyl)-(S,S)-1,2-diphenyl-1,2-diaminoethane / CH₂Cl₂ / -90 °C

6: H₂ / Pd(OH)2 on C / ethyl acetate / Ambient temperature

7: hydrochlorid acid / 0 °C

8: Et₃N, DMAP / CH₂Cl₂ / -60 °C

9: (n-Bu₄N)N₃ / CH₂Cl₂ / -78 deg C to room temperature

10: H₂ / Pd on C / ethyl acetate / Ambient temperature

12: 42 percent / potassium tert-butoxide / tetrahydrofuran / Heating

With hydrogenchloride; dmap; osmium(VIII) oxide; 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; potassium tert-butylate; hydrogen; tetrabutylammoniun azide; triethylamine; palladium on activated charcoal; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1021/jo00301a007