(2S,3R)-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-ol

Base Information

• Chemical Name: (2S,3R)-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-ol
• CAS No.: 207226-48-0
• Molecular Formula: C₃₄H₅₂O₆Si
• Molecular Weight: 584.869

Synonyms:(2S,3R)-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-ol

Chemical Property of (2S,3R)-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-ol

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Technology Process of (2S,3R)-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-ol

There total 39 articles about (2S,3R)-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-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: 84.0%

(3'R,4'S,5'S,6'R,7'R,8'R)-3'-hydroxy-5',7'-O-isopropylidene-4',6',8'-trimethyl-9'-[(tert-butyldiphenylsilyl)oxy]-non-1'-enyl-1,3-dioxolane (209251-49-0) → (2S,3R)-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-ol (207226-48-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In benzene; at 23 ℃; for 16h;

DOI:10.1021/jo0267908

Reference yield: 84.0%

(E)-(3R,4S)-4-{(4S,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-1-[1,3]dioxolan-2-yl-pent-1-en-3-ol → (2S,3R)-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-ol (207226-48-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In benzene;

DOI:10.1021/jo980387c

Reference yield: 72.0%

(2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-one (359849-33-5) → (2S,3R)-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-ol (207226-48-0)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 - -50 ℃; for 3h;

DOI:10.1021/jo010310f

upstream raw materials:

2-bromo-2-(2-ethyl)dioxolane

(R)-2-{(4R,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde

(2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-one

1,3-dioxolan-2-ylethylmagnesium bromide

Downstream raw materials:

(2S,3R)-3-benzyloxymethoxy-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentane

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