(2R,4S,5R)-(-)-4-(t-butyldimethylsiloxymethyl)-2-phenyl-1,3-dioxan-5-yl bromoacetate

Base Information

• Chemical Name: (2R,4S,5R)-(-)-4-(t-butyldimethylsiloxymethyl)-2-phenyl-1,3-dioxan-5-yl bromoacetate
• CAS No.: 121194-86-3
• Molecular Formula: C₁₉H₂₉BrO₅Si
• Molecular Weight: 445.426

Synonyms:(2R,4S,5R)-(-)-4-(t-butyldimethylsiloxymethyl)-2-phenyl-1,3-dioxan-5-yl bromoacetate

Chemical Property of (2R,4S,5R)-(-)-4-(t-butyldimethylsiloxymethyl)-2-phenyl-1,3-dioxan-5-yl bromoacetate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2R,4S,5R)-(-)-4-(t-butyldimethylsiloxymethyl)-2-phenyl-1,3-dioxan-5-yl bromoacetate

There total 3 articles about (2R,4S,5R)-(-)-4-(t-butyldimethylsiloxymethyl)-2-phenyl-1,3-dioxan-5-yl bromoacetate 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: 70.0%

1,3-O-benzylidene-4-O-(tert-butyldimethylsilyl)-L-erythritol (121194-85-2) + 2-Bromoacetyl bromide (598-21-0) → (2R,4S,5R)-(-)-4-(t-butyldimethylsiloxymethyl)-2-phenyl-1,3-dioxan-5-yl bromoacetate (121194-86-3)

Guidance literature:

With pyridine; In dichloromethane; for 5.5h; Ambient temperature;

Reference yield:

(2R,4S,5R)-2-phenyl-5-hydroxy-1,3-dioxane-4-methanol (117122-84-6) → (2R,4S,5R)-(-)-4-(t-butyldimethylsiloxymethyl)-2-phenyl-1,3-dioxan-5-yl bromoacetate (121194-86-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / Et₃N, 4-dimethylaminopyridine / dimethylformamide

2: 70 percent

With dmap; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)80437-2

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2R,4S,5R)-(-)-4-(t-butyldimethylsiloxymethyl)-2-phenyl-1,3-dioxan-5-yl bromoacetate (121194-86-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / Et₃N, 4-dimethylaminopyridine / dimethylformamide

2: 70 percent

With dmap; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)80437-2

upstream raw materials:

1,3-O-benzylidene-4-O-(tert-butyldimethylsilyl)-L-erythritol

2-Bromoacetyl bromide

(2R,4S,5R)-2-phenyl-5-hydroxy-1,3-dioxane-4-methanol

tert-butyldimethylsilyl chloride

Downstream raw materials:

(Triphenyl-λ⁵-phosphanylidene)-acetic acid (2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-[1,3]dioxan-5-yl ester

(6R,7R,8S,8aR,2'R,4'S,5'R)-(+)-4'-(t-butyldimethylsiloxymethyl)-2'-phenyl-1',3'-dioxan-5'-yl 6,7-bis-(3,4-dimethoxyphenyl)-5-oxoindolizidine-8-carboxylate

(6S,7R,8S,8aR)-6,7-Bis-(3,4-dimethoxy-phenyl)-5-oxo-octahydro-indolizine-8-carboxylic acid (2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-[1,3]dioxan-5-yl ester

(E)-6-[(E)-2,3-Bis-(3,4-dimethoxy-phenyl)-acryloylamino]-hex-2-enoic acid (2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-[1,3]dioxan-5-yl ester

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