((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: ((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane
• CAS No.: 909781-96-0
• Molecular Formula: C₃₆H₄₆O₅Si
• Molecular Weight: 586.844

Synonyms:((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Chemical Property of ((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

There total 1 articles about ((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane 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%

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(prop-2-ynyl)-tetrahydro-pyran-3-ol (273925-99-8) → ((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane (909781-96-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1016/j.tetlet.2006.05.170

Reference yield: 73.0%

((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane (909781-96-0) + (2'S,3'S)-3'-(tert-butyldimethylsiloxy)-tetrahydropyran-2'-carbaldehyde (125877-83-0) → (S)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-ol (909781-97-1) + (R)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

Guidance literature:

((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane; With n-butyllithium; In tetrahydrofuran; at -80 ℃;

(2'S,3'S)-3'-(tert-butyldimethylsiloxy)-tetrahydropyran-2'-carbaldehyde; In tetrahydrofuran; at -80 - -20 ℃;

DOI:10.1016/j.tetlet.2006.05.170

Reference yield:

((2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane (909781-96-0) → (2R,4aR,5aS,6aR,7aS,11aR,12R,12aS,13aR,14R,14aS)-2-Phenyl-tetradecahydro-1,3,5,7,11,13-hexaoxa-pentacene-12,14-diol (909782-13-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran / -80 °C

1.2: 73 percent / tetrahydrofuran / -80 - -20 °C

2.1: 96 percent / DMAP; pyridine

3.1: 73 percent / RuO₂; NaIO₄ / CCl₄; acetonitrile; H₂O

4.1: 96 percent / CSA / methanol; CH₂Cl₂

5.1: 91 percent / Et₃SiH; TMSOTf / acetonitrile; CH₂Cl₂ / -40 - 0 °C

6.1: H₂ / Pd(OH)2 / ethyl acetate; methanol

7.1: CSA / dimethylformamide

8.1: K₂CO₃ / methanol

With pyridine; triethylsilane; dmap; ruthenium(IV) oxide; sodium periodate; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; potassium carbonate; palladium dihydroxide; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.tetlet.2006.05.170

upstream raw materials:

tert-butyldimethylsilyl chloride

(2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(prop-2-ynyl)-tetrahydro-pyran-3-ol

Downstream raw materials:

(S)-4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-1-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-yn-1-ol

(2R,4aR,5aS,6aR,7aS,11aR,12R,12aS,13aR,14R,14aS)-2-Phenyl-tetradecahydro-1,3,5,7,11,13-hexaoxa-pentacene-12,14-diol

(2R,4aR,5aS,6aR,7aS,11aS,12R,12aR,13aS,14R,14aR)-12,14-Bis-allyloxy-2-phenyl-tetradecahydro-1,3,5,7,11,13-hexaoxa-pentacene

(2R,3R,4S,4aS,5aS,6R,6aR,10aS,11aR,12aS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-dodecahydro-1,5,7,11-tetraoxa-naphthacene-5a,6,11a-triol

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