(2S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-ol

Base Information

• Chemical Name: (2S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-ol
• CAS No.: 82707-03-7
• Molecular Formula: C₂₅H₃₄O₄Si
• Molecular Weight: 426.628
• Mol file: 82707-03-7.mol

Synonyms:(2S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-ol

Chemical Property of (2S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-ol

There total 10 articles about (2S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-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:

Methyl 4,6-O-Benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside (75879-81-1) → (2S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-ol (82707-03-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / DMAP / CH₂Cl₂

2: aq. 50percent AcOH

3: pyridine / 18 h / 0 °C

4: COCl₂, Me₂SO, Et₃N / CH₂Cl₂ / -60 deg C -> 25 deg C

5: KCN / methanol

With pyridine; dmap; potassium cyanide; acetic acid; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ja00386a076

Reference yield:

methyl 3-O-acetyl-4,6-O-benzylidene-2-C-methyl-α-D-allopyranoside (82707-13-9) → (2S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-ol (82707-03-7)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. 50percent AcOH

2: pyridine / 18 h / 0 °C

3: COCl₂, Me₂SO, Et₃N / CH₂Cl₂ / -60 deg C -> 25 deg C

4: KCN / methanol

With pyridine; potassium cyanide; acetic acid; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ja00386a076

Reference yield:

Acetic acid (2R,3S,4S,5R,6S)-3-hydroxy-2-hydroxymethyl-6-methoxy-5-methyl-tetrahydro-pyran-4-yl ester → (2S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-methyl-3-methylene-tetrahydro-pyran-4-ol (82707-03-7)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 18 h / 0 °C

2: COCl₂, Me₂SO, Et₃N / CH₂Cl₂ / -60 deg C -> 25 deg C

3: KCN / methanol

With pyridine; potassium cyanide; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ja00386a076

upstream raw materials:

Methyltriphenylphosphonium bromide

methyl 3-O-acetyl-6-O-t-butyldiphenylsilyl-2-deoxy-2-C-methyl-α-D-ribo-hexapyranoside-3-ulose

Methylenetriphenylphosphorane

Methyl 4,6-O-Benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside

Downstream raw materials:

tert-Butyl-((2S,3R,4R,5R,6S)-6-methoxy-4-methoxymethoxy-3,5-dimethyl-tetrahydro-pyran-2-ylmethoxy)-diphenyl-silane

tert-Butyl-((2S,3S,4R,5R,6S)-6-methoxy-4-methoxymethoxy-3,5-dimethyl-tetrahydro-pyran-2-ylmethoxy)-diphenyl-silane

(4S,6R)-4-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-((Z)-(3S,4R,5S)-4-hydroxy-3,5-dimethyl-hept-1-enyl)-tetrahydro-pyran-2-ol

(4S,6R)-4-Benzyloxy-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-((3S,4R,5S)-4-hydroxy-3,5-dimethyl-hept-1-ynyl)-tetrahydro-pyran-2-ol