tert-Butyl-[(S)-1-(4-methoxy-benzyloxymethyl)-3-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-but-3-enyloxy]-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-[(S)-1-(4-methoxy-benzyloxymethyl)-3-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-but-3-enyloxy]-dimethyl-silane
• CAS No.: 206272-61-9
• Molecular Formula: C₄₇H₆₂O₈Si
• Molecular Weight: 783.09
• Mol file: 206272-61-9.mol

Synonyms:tert-Butyl-[(S)-1-(4-methoxy-benzyloxymethyl)-3-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-but-3-enyloxy]-dimethyl-silane

Chemical Property of tert-Butyl-[(S)-1-(4-methoxy-benzyloxymethyl)-3-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-but-3-enyloxy]-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[(S)-1-(4-methoxy-benzyloxymethyl)-3-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-but-3-enyloxy]-dimethyl-silane

There total 5 articles about tert-Butyl-[(S)-1-(4-methoxy-benzyloxymethyl)-3-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-but-3-enyloxy]-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:

(S)-2-[(4-methoxybenzyloxy)methyl]oxirane (80910-01-6,108836-41-5,134733-19-0,144069-33-0) → tert-Butyl-[(S)-1-(4-methoxy-benzyloxymethyl)-3-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-but-3-enyloxy]-dimethyl-silane (206272-61-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

2: 100 percent / 2,6-lutidine / CH₂Cl₂

3: 1.) n-BuLi / 1.) THF, HMPA, -78 deg C, 2.) THF, HMPA

4: 1.) n-BuLi, 2.) i-PrMgCl / 1.) THF, HMPA, -78 deg C, 2.) THF, HMPA

With 2,6-dimethylpyridine; n-butyllithium; isopropylmagnesium chloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1016/S0960-894X(98)00050-X

Reference yield:

p-methoxybenzyl chloride (824-94-2) → tert-Butyl-[(S)-1-(4-methoxy-benzyloxymethyl)-3-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-but-3-enyloxy]-dimethyl-silane (206272-61-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / NaH, Bu₄NI

2: 100 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

3: 100 percent / 2,6-lutidine / CH₂Cl₂

4: 1.) n-BuLi / 1.) THF, HMPA, -78 deg C, 2.) THF, HMPA

5: 1.) n-BuLi, 2.) i-PrMgCl / 1.) THF, HMPA, -78 deg C, 2.) THF, HMPA

With 2,6-dimethylpyridine; n-butyllithium; isopropylmagnesium chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1016/S0960-894X(98)00050-X

Reference yield:

(S)-4-Benzenesulfonyl-1-(4-methoxy-benzyloxy)-butan-2-ol (200186-41-0) → tert-Butyl-[(S)-1-(4-methoxy-benzyloxymethyl)-3-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-but-3-enyloxy]-dimethyl-silane (206272-61-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / 2,6-lutidine / CH₂Cl₂

2: 1.) n-BuLi / 1.) THF, HMPA, -78 deg C, 2.) THF, HMPA

3: 1.) n-BuLi, 2.) i-PrMgCl / 1.) THF, HMPA, -78 deg C, 2.) THF, HMPA

With 2,6-dimethylpyridine; n-butyllithium; isopropylmagnesium chloride; In dichloromethane;

DOI:10.1016/S0960-894X(98)00050-X

upstream raw materials:

diiodomethane

[(S)-3-Benzenesulfonyl-1-(4-methoxy-benzyloxymethyl)-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-butoxy]-tert-butyl-dimethyl-silane

(S)-2-[(4-methoxybenzyloxy)methyl]oxirane

p-methoxybenzyl chloride

Downstream raw materials:

tert-Butyl-dimethyl-{(E)-(S)-1-[2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-allyl]-penta-2,4-dienyloxy}-silane

(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-pent-4-enal

(S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-pent-4-en-1-ol