methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl 2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside

Base Information

• Chemical Name: methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl 2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside
• CAS No.: 82707-04-8
• Molecular Formula: C₃₂H₄₂O₄Si
• Molecular Weight: 518.769
• Mol file: 82707-04-8.mol

Synonyms:methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl 2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside

Chemical Property of methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl 2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl 2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside

There total 14 articles about methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl 2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside 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%

benzyl bromide (100-39-0) + (2S,3R,4R,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-3,5-dimethyl-tetrahydro-pyran-4-ol (87318-99-8) → methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl 2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside (82707-04-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; for 6h; Ambient temperature;

DOI:10.1055/s-1999-3671

Reference yield:

Methyl 4,6-O-Benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside (75879-81-1) → methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl 2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside (82707-04-8)

Guidance literature:

Multi-step reaction with 6 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

6: 1.) 20percent Pd(OH)2/C₂H₂, 2.) KH / 1.) dioxane, 2.) THF

With pyridine; dmap; potassium cyanide; palladium dihydroxide; potassium hydride; acetic acid; dimethyl sulfoxide; triethylamine; acetylene; 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 → methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl 2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside (82707-04-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 18 h / 0 °C

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

3: KCN / methanol

4: 1.) 20percent Pd(OH)2/C₂H₂, 2.) KH / 1.) dioxane, 2.) THF

With pyridine; potassium cyanide; palladium dihydroxide; potassium hydride; dimethyl sulfoxide; triethylamine; acetylene; In methanol; dichloromethane;

DOI:10.1021/ja00386a076

upstream raw materials:

benzyl bromide

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

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

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

Downstream raw materials:

(2S,3S,4R,6S,7R,8S,9S)-3-Benzyloxy-10-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-9-methoxy-2,4,6,8-tetramethyl-1-trityloxy-decan-5-one

(2S,3S,4R,6R,7S,8S,9S)-3-Benzyloxy-10-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-9-methoxy-2,4,6,8-tetramethyl-1-trityloxy-decan-5-one

3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-5-O-methylsulfonyl-1-O-triphenylmethyl-D-gulitol

((2S,3R,4R,5R,6S)-4-Benzyloxy-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-{2-[(1R,2S)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-1-methyl-propyl]-[1,3]dithian-2-yl}-methanone